Acetic Anhydride → 4-[1-(acetyloxy)-4,4-dimethyl-2-octenyl]-hexahydro-5-methyl-2H-cyclopenta[b]furan-2-one

HRID 1607744Notes

Reaction equation

HRID 1607744 reaction equation
[OH:1][CH:2]([CH:12]1[CH:19]2[CH:15]([O:16][C:17](=[O:20])[CH2:18]2)[CH2:14][CH:13]1[CH3:21])[CH:3]=[CH:4][C:5]([CH3:11])([CH3:10])[CH2:6][CH2:7][CH2:8][CH3:9].[C:22](OC(=O)C)(=[O:24])[CH3:23]>CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[C:22]([O:1][CH:2]([CH:12]1[CH:19]2[CH:15]([O:16][C:17](=[O:20])[CH2:18]2)[CH2:14][CH:13]1[CH3:21])[CH:3]=[CH:4][C:5]([CH3:10])([CH3:11])[CH2:6][CH2:7][CH2:8][CH3:9])(=[O:24])[CH3:23]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 731845934-[1-(hydroxy)-4,4-dimethyl-2-octenyl]hexahydro-5-methyl-2H-cyclopenta[b]furan-2-one

Product 1

HCID 727270464-[1-(acetyloxy)-4,4-dimethyl-2-octenyl]-hexahydro-5-methyl-2H-cyclopenta[b]furan-2-one

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Following the procedure of example VII, 48.9 g, of crude, optically active [3aR-[3a alpha,4alpha(1S*,2E), 5beta,6a alpha-]]-4-[1-(hydroxy)-4,4-dimethyl-2-octenyl]hexahydro-5-methyl-2H-cyclopenta[b]furan-2-one was acetylated with 60 ml of acetic anhydride and 0.5 g of 4-dimethylaminopyridine in 400 ml of ethyl acetate. The product was crystallized from 60 ml of hexane giving 30.05 g of optically active [3aR-[3alpha,4alpha(1S*,2E),5beta,6a alpha-]]-4-[1-(acetyloxy)-4,4-dimethyl-2-octentyl]-hexahydro- 5-methyl-2H-cyclopenta[b]furan-2-one in colorless crystals with mp 83°-83.5°.

Workup

  1. customThe product was crystallized from 60 ml of hexane giving 30.05 g of optically active [3aR-[3alpha,4alpha(1S*,2E),5beta,6a alpha-]]-4-[1-(acetyloxy)-4,4-dimethyl-2-octentyl]-hexahydro- 5-methyl-2H-cyclopenta[b]furan-2-one in colorless crystals with mp 83°-83.5°

Sources & evidence

ORD record
ord-b40eaaad09ff421a828eb5547f37c9c7
Source dataset
uspto-grants-1989_09
Patent number
US04866205

Reaction notes

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