Acetic Acid → Methyl 2-acetyl-5-oxocyclopentane-1-carboxylate

HRID 1634584Notes

Reaction equation

C[O:2][C:3]([C:5]12CC1C[CH2:7][C:6]2=O)=O.[C:12]([O-:15])(=[O:14])[CH3:13].[K+].[C:17]([OH:20])(=O)[CH3:18].[CH3:21]S(C)=O>>[CH3:21][O:14][C:12]([CH:13]1[CH:7]([C:17](=[O:20])[CH3:18])[CH2:6][CH2:5][C:3]1=[O:2])=[O:15]

Participants

Reactant 4

HCID 176Acetic Acid

HCID 679Dimethyl Sulfoxide

HCID 517044Potassium Acetate

HCID 12881134Methyl 2-oxobicyclo[3.1.0]hexane-1-carboxylate

Product 1

HCID 13213561Methyl 2-acetyl-5-oxocyclopentane-1-carboxylate

Procedure

Tanomori et al., Biosci. Biotech. Biochem. 1995, 59: 2091-2093, discloses the reaction of 1-methoxycarbonyl-2-oxo-bicyclo[3.1.0]hexane with potassium acetate and acetic acid in dimethylsulfoxide at 90° C. (4 hours) to obtain 2-methoxycarbonyl-3-acetyl-cyclopentanone. The reference further discloses a formal total synthesis of (+)-carbovir by conversion of the cyclopentanone.

Sources & evidence

ORD record: ord-cfd2189ba5ef4e889a92c1466419519b
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06506908B2

Reaction notes

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