Benzene → HCID 15814063, compound

Reaction equation

[C:1]([Br:4])(=[O:3])C.[C:5]([O:8][CH2:9][C@@H:10]1[C@@H:14]([CH2:15][O:16][C:17](=[O:19])[CH3:18])[O:13][CH2:12][O:11]1)(=[O:7])[CH3:6].[CH:20]1C=CC=CC=1>[Cl-].[Zn+2].[Cl-]>[Br:4][CH2:1][O:3][C@@H:10]([C@H:14]([O:13][C:12](=[O:11])[CH3:20])[CH2:15][O:16][C:17](=[O:19])[CH3:18])[CH2:9][O:8][C:5](=[O:7])[CH3:6]

Participants

Procedure

A mixture of 25.0 g of acetyl bromide and 42.0 g of (4R,5R)-4,5-bis(acetoxymethyl)-1,3-dioxolane obtained in Example 4 was stirred under cooling with ice, and 1.0 g of anhydrous zinc chloride was added to it. After the reaction for 30 minutes, the ice water bath was dismantled and the mixture was stirred for a further one hour while stirring at room temperature. After the reaction, 50 ml of benzene was added to separate insoluble matters by filtration, and the benzene was evaporated at a low temperature (below room temperature). No peaks for the raw material were observed at all by NMR analysis of the reaction product, indicating that the decylization occurred quantitatively and the title compound was produced.