1-Phenylethanol → Acetate

HRID 1291985Notes

Reaction equation

HRID 1291985 reaction equation
[C:1]1([CH:7]([OH:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:10]([O:13]C=COCC)(=[O:12])[CH3:11]>CCCCCC>[C:1]1([CH:7]([OH:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:10]([O-:13])(=[O:12])[CH3:11]

Participants

5

Reactant 2

HCID 74091-PhenylethanolHCID 548203HCID 548203, compound

Product 2

HCID 175AcetateHCID 74091-Phenylethanol

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

1-Phenylethanol (100 mg) was dissolved in a 10% solution of ethoxyvinyl acetate in hexane (2 ml), followed by addition of lipase PS (10 mg). After about 3 hours at room temperature, 50% conversion was observed by TLC. The alcohol and acetate were isolated using flash chromatography on silica gel 60 using a 1:10 to 1:1 gradient of ethyl acetate in hexane. The isolated yield of the acetate was 40%, corresponding to 80% of the theoretical maximum at 50% conversion, and that of the alcohol 39%. The enantiomeric excess (ee) of the acetate was >95% (determined by 1H-NMR, chiral shift experiment with Eu(hfc)3, 10 mg of acetate, 40 mg of shift reagent); αD +103.5° (c=1, MeOH).

Workup

  1. additionfollowed by addition of lipase PS (10 mg)

Sources & evidence

ORD record
ord-4322e3caf1994e0cabac458e4f22cf10
Source dataset
uspto-grants-1998_05
Patent number
US05756321

Reaction notes

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