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 (5.293 g) in pentane (100 ml) was added vinyl acetate (11.38 ml) and Lipase PS (AMANO SEIYAKU Co., Ltd.) (1.235 g) and then shaken for 72 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=5:2) to give (R)-methyl 9-hydroxy-10-undecenate (1.937 g, 36.7%).
Workup
- filtrationThe reaction mixture was filtrated
- additionthe filtrate was poured into ethyl acetate
- washwashed 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=5:2)
Sources & evidence
- ORD record
- ord-c58c0209191e44388d942b4c58606e20
- Source dataset
- uspto-grants-2003_08
- Patent number
- US06605741B2
Reaction notes
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