Vinyl Acetate → (R)-methyl 9-hydroxy-10-undecenate
Reaction equation
[OH:1][CH:2]([CH:14]=[CH2:15])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11].C(OC=C)(=O)C>CCCCC>[OH:1][C@@H:2]([CH:14]=[CH2:15])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 30 °C
Procedure
To a solution of methyl 9-hydroxy-10-undecenate (509 mg) in pentane (12 ml) was added vinyl acetate (1.097 ml) and Lipase PS (AMANO SEIYAKU Co., Ltd.) (238 mg) and then shaken for 62 hours at 30° C. The reaction mixture was filtrated and the filtrate was poured into ethyl acetate, washed with saturated brine, dried over magnesium sulfate anhydride, and then evaporated under reduced pressure. The resulting product was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1) to give (R)-methyl 9-hydroxy-10-undecenate (168 mg, 33.6%).