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>C(OC(C)C)(C)C>[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 (500 mg) in diisopropyl ether (12 ml) was added vinyl acetate (323 μl) and Lipase PS (AMANO SEIYAKU Co., Ltd.) (500 mg) and then shaken for 62 hours at 30° C. The reaction mixture was filtrated and the filtrate was poured into ethyl acetate. The organic layer was 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 (152 mg, 30.4%).
Workup
- filtrationThe reaction mixture was filtrated
- additionthe filtrate was poured into ethyl acetate
- washThe organic layer was washed with saturated brine
- dry with materialdried over magnesium sulfate anhydride
- customevaporated under reduced pressure
- customThe resulting product was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1)
Sources & evidence
- ORD record
- ord-b46dbf12afe94e36857135fb52f2566b
- Source dataset
- uspto-grants-2003_08
- Patent number
- US06605741B2
Reaction notes
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