Isopropenyl acetate → HCID 53866555, compound

HRID 274081Notes

Reaction equation

HRID 274081 reaction equation
[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]2[CH2:7][CH2:8][CH2:9][CH:10]([OH:12])[CH2:11][C:5]=2[CH:4]=1.[C:15](OC(C)=C)(=[O:17])[CH3:16]>C(OC(C)C)(C)C>[C:15]([O:12][C@@H:10]1[CH2:9][CH2:8][CH2:7][C:6]2[CH:13]=[CH:14][C:3]([O:2][CH3:1])=[CH:4][C:5]=2[CH2:11]1)(=[O:17])[CH3:16]

Participants

4

Reactant 2

HCID 7916Isopropenyl acetateHCID 200947203-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-ol

Product 1

HCID 53866555HCID 53866555, compound

Reagents, catalysts & solvents 1

HCID 7914Diisopropyl EtherSolvent

Procedure

A mixture of (RS)-3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-ol (221 g), isopropenyl acetate (380 ml) and lipase PS (Amano) (221 g) in diisopropyl ether (4.8 l) was stirred at ambient temperature for 4 days. The reaction mixture was filtrated (celite) and evaporated under reduced pressure. The residue was purified by flash chromatography (silica gel, using dichloromethane and dichloromethane-methanol (20:1) successively as eluents). The first eluate gave (R)-3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl acetate (138.2 g) as a pale yellow oil and the second eluate (S)-3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-ol (104.4 g) as a colorless powder.

Workup

  1. filtrationThe reaction mixture was filtrated (celite)
  2. customevaporated under reduced pressure
  3. customThe residue was purified by flash chromatography (silica gel

Sources & evidence

ORD record
ord-b826aa3eb00e456293b47d0a54cf5d0b
Source dataset
uspto-grants-1995_02
Patent number
US05387710

Reaction notes

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