Vinyl Acetate → HCID 56590408, compound

HRID 2406863Notes

Reaction equation

HRID 2406863 reaction equation
[C:1]([C:4]1[CH2:8][CH2:7][CH:6]([OH:9])[CH:5]=1)([CH3:3])=[CH2:2].[C:10]([O:13][CH:14]=[CH2:15])(=[O:12])[CH3:11]>CC(OC)(C)C>[C:1]([C:4]1[CH2:8][CH2:7][C@H:6]([OH:9])[CH:5]=1)([CH3:3])=[CH2:2].[C:1]([C:4]1[CH2:5][CH2:6][C@@H:14]([O:13][C:10](=[O:12])[CH3:11])[CH:15]=1)([CH3:3])=[CH2:2]

Participants

5

Reactant 2

HCID 7904Vinyl AcetateHCID 14874553HCID 14874553, compound

Product 2

HCID 56590408HCID 56590408, compoundHCID 56590409HCID 56590409, compound

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
40 °C

Procedure

Compound (1a*) (63.9 mg, 0.5146 mmol) was dissolved in anhydrous MTBE (1.7 mL) and lipase PS (20 w %, 12.9 mg) and vinyl acetate (31 μL, 0.3363 mmol) were added before the resulting mixture was heated to 40° C. for 18 hours. Solids were removed by filtration and the filtrate concentrated in vacuo. Purification by chromatography (hexane/EtOAc 10/1 to 5/1 to 3/1 to 1/1) using Merck aluminium oxide 90 (0.063-0.200 mm, 70-230 mesh) furnished 25.7 mg of compound 7a as white solid with 40% yield and 43.4 mg of the enantioenriched acetic acid (R)-3-isopropenyl-cyclopent-2-enyl ester as slightly yellow oil with 51% yield.

Workup

  1. customSolids were removed by filtration
  2. concentrationthe filtrate concentrated in vacuo
  3. customPurification by chromatography (hexane/EtOAc 10/1 to 5/1 to 3/1 to 1/1)

Sources & evidence

ORD record
ord-520845d4e48147a5a18a3db245f0176d
Source dataset
uspto-grants-2014_08
Patent number
US08809395B2

Reaction notes

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