Methyl tetrahydro-4-methyl-3-oxo-2-thiophenecarboxylate → Ethyl 5,5-dimethyl-3-oxothiolane-2-carboxylate

HRID 1657637Notes

Reaction equation

HRID 1657637 reaction equation
CC1CSC(C(OC)=O)C1=O.[CH3:12][C:13]([CH3:27])([CH2:21][C:22]([O:24]CC)=[O:23])[S:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].CC(C)([O-])C.[K+]>>[CH3:12][C:13]1([CH3:27])[S:14][CH:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:22](=[O:23])[CH2:21]1.[CH3:12][CH:13]1[S:14][CH:15]([C:16]([O-:18])=[O:17])[C:22](=[O:24])[CH2:21]1

Participants

5

Reactant 3

HCID 10487456Methyl tetrahydro-4-methyl-3-oxo-2-thiophenecarboxylateHCID 12716248Ethyl 3-[(2-ethoxy-2-oxoethyl)sulfanyl]-3-methylbutanoateHCID 23665647Potassium tert-butoxide

Product 2

HCID 12716257Ethyl 5,5-dimethyl-3-oxothiolane-2-carboxylateHCID 215199965-Methyl-3-oxo-tetrahydrothiophene-2-carboxylate

Procedure

The keto esters, alkyl 4-oxo-2,3,4,5-tetrahydrothiophene-3-carboxylate and alkyl 3-oxo-2,3,4,5-tetrahydrothiophene-2-carboxylate may be prepared by the procedure of Woodward and Eastman, J. Am. Chem. Soc. 68, 2229 (1946); alkyl 4-oxo-2,3,5,6-tetrahydro-4H-thiopyran-3-carboxylate by the method of G.M. Bennett and L. V. D. Scorah, J. Chem. Soc., 194, (1927); and alkyl 3-oxo-2,3,4,5-tetrahydro-6H-thiopyran-2-carboxylate by the procedure of Leonard and Figueras, J. Chem. Soc., 74, 917 (1952). Methyl 4-methyl-3-oxo-tetrahydrothiophene-2-carboxylate is disclosed in Chemical Abstracts, 63, 5491 (1965). Ethyl 5,5-dimethyl-3-oxo-tetrahydrothiophene-2-carboxylate is prepared by reacting diethyl 4,4-dimethyl-3-thiahexanedioate with potassium tertiary butoxide. 5-methyl-3-oxo-tetrahydrothiophene-2-carboxylate is formed by reacting diethyl 4-methyl-3-thiahexanedioate with potassium tertiary butoxide.

Sources & evidence

ORD record
ord-3695f762ca1647808a89e8b62b71b81d
Source dataset
uspto-grants-1976_06
Patent number
US03960871

Reaction notes

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