Title:
METHOD FOR PRODUCING α-ALLYLATION CYCLOALKANONE
Document Type and Number:
WIPO Patent Application WO/2020/189661
Kind Code:
A1
Abstract:
The purpose of the present invention is to provide a method for obtaining an α-allylation cycloalkanone using a cyclic compound cycloalkanone as a starting material. Provided is a method for producing an α-allylation cycloalkanone represented by general formula (III), the method comprising step 1: a step for reacting a compound represented by general formula (I) with a C1-4 alcohol in the presence of a first acid catalyst and optionally a dehydrating agent, and step 2: a step for reacting a crude product obtained in step 1 with a compound represented by general formula (II) in the presence of a second acid catalyst to obtain an α-allylation cycloalkanone represented by general formula (III), step 1 and step 2 being sequentially performed. [In the formulae, the group –A1- (the left dangling bond refers to a dangling bond to be associated with carbon atom C1, and the right dangling bond refers to a dangling bond to be associated with carbon atom C2) is a C4-20 alkylene group which may optionally include a hetero atom, and may optionally have a substituent; and R4 is a hydrogen atom or a C1-4 alkyl group.]
Inventors:
DEGUCHI JUN
SAKAKIBARA MAKOTO
SAKODA DAICHI
SAKAKIBARA MAKOTO
SAKODA DAICHI
Application Number:
PCT/JP2020/011627
Publication Date:
September 24, 2020
Filing Date:
March 17, 2020
Export Citation:
Assignee:
KAO CORP (JP)
International Classes:
C07C45/45; C07C45/61; C07C49/385; C07C49/413; C07C49/587; C07B61/00
Domestic Patent References:
| WO2015036402A1 | 2015-03-19 |
Foreign References:
| JPS632946A | 1988-01-07 | |||
| JP2014500237A | 2014-01-09 | |||
| US20120088935A1 | 2012-04-12 | |||
| FR2645530A1 | 1990-10-12 | |||
| JP2015533799A | 2015-11-26 | |||
| JP2016034937A | 2016-03-17 | |||
| JP2002105010A | 2002-04-10 |
Other References:
VITALI ROMANO; GARDI RINALDO: "Alkylation of steroids by the Claisen rearrangement of allyl ethers. II. Rearrangement of 17-oxo steroid enol ethers", GAZZETTA CHIMICA ITALIANA, vol. 95, no. 4, 30 November 1964 (1964-11-30), IT, pages 351 - 367, XP009530361, ISSN: 0016-5603
XX: "Jikken Kagaku Koza 20 Yuki Gosei II", 30 November 1991, XX , Japan , ISBN: 4-621-03728-5, article CHEMICAL SOCIETY OF JAPAN: "Passage; Experiment chemistry lecture 20: Organic synthesis II -alcohol, amine-", pages: 245 - 252, XP009530362
DUBS, P. ET AL.: "Novel Synthesis of a [10](2,6)Pyridinophane, a Structural Isomer of Muscopyridine", J. C. S. CHEM. COMM., 1976, pages 1021, XP055742750
WHOL R. A.: "A Convenient One-Step Procedure for the Synthesis of Cyclic Enol Ethers. The Preparation of 1-Methoxy-1-cycloalkenes.", SYNTHESIS, 1974, pages 38 - 40, XP055742751
RAUTENSTRAUCH, V. ET AL.: "A Short Synthesis of (±)-Muscone", HELVETICA CHIMICA ACTA, vol. 73, 1990, pages 896 - 901, XP055846495
SUGIURA, M. ET AL.: "Regiochemical Control in the Pd(II)-Catalyzed Claisen Rearrangement via In Situ Enol Ether Exchange", TETRAHEDRON LETTERS, vol. 37, no. 44, 1996, pages 7991 - 7994, XP004031024, DOI: 10.1016/0040-4039(96)01790-X
W. L. HOWARDN. B. LORETTE, ORGANIC SYNTHESIS, vol. 5, 1973, pages 292
See also references of EP 3943477A4
XX: "Jikken Kagaku Koza 20 Yuki Gosei II", 30 November 1991, XX , Japan , ISBN: 4-621-03728-5, article CHEMICAL SOCIETY OF JAPAN: "Passage; Experiment chemistry lecture 20: Organic synthesis II -alcohol, amine-", pages: 245 - 252, XP009530362
DUBS, P. ET AL.: "Novel Synthesis of a [10](2,6)Pyridinophane, a Structural Isomer of Muscopyridine", J. C. S. CHEM. COMM., 1976, pages 1021, XP055742750
WHOL R. A.: "A Convenient One-Step Procedure for the Synthesis of Cyclic Enol Ethers. The Preparation of 1-Methoxy-1-cycloalkenes.", SYNTHESIS, 1974, pages 38 - 40, XP055742751
RAUTENSTRAUCH, V. ET AL.: "A Short Synthesis of (±)-Muscone", HELVETICA CHIMICA ACTA, vol. 73, 1990, pages 896 - 901, XP055846495
SUGIURA, M. ET AL.: "Regiochemical Control in the Pd(II)-Catalyzed Claisen Rearrangement via In Situ Enol Ether Exchange", TETRAHEDRON LETTERS, vol. 37, no. 44, 1996, pages 7991 - 7994, XP004031024, DOI: 10.1016/0040-4039(96)01790-X
W. L. HOWARDN. B. LORETTE, ORGANIC SYNTHESIS, vol. 5, 1973, pages 292
See also references of EP 3943477A4
Attorney, Agent or Firm:
IKEUCHI & PARTNERS (JP)
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