PURPOSE: To obtain an optically active 1-deuterated substance useful as a intermediate for perfume, drugs and liquid crystal compounds, by reacting (R)-5- benzyloxy-4-hydroxy-1-pentyne with deuterated DMSO in the presence of a base.
CONSTITUTION: A compound shown by formula I or formula II (R is protecting group; asterisk is asymmetric carbon atom.) is reacted with deuterated DMSO in the presence of a base (e.g. potassium tertiary butoxide) at room temperature to give a compound shown by formula III (X1WX3 are H or heavy hydrogen and at least one of X1WX3 is heavy hydrogen). Since deuterated DMSO is also useful as a reaction solvent and preferably used in an extremely excess amount. After the reaction is over, treatment with heavy water increases yield of the aimed substance and improves substitution ratio of heavy hydrogen.
OGASAWARA KUNIRO
SEKIGUCHI YOSHIISA
