Methyl 4-[(2-methoxy-2-oxoethyl)sulfanyl]butanoate → Methyl 3-oxotetrahydrothiopyran-2-carboxylate

HRID 2299102Notes

Reaction equation

HRID 2299102 reaction equation
CC(C)([O-])C.[K+].[CH3:7][O:8][C:9](=[O:19])[CH2:10][S:11][CH2:12][CH2:13][CH2:14][C:15](OC)=[O:16]>C(OCC)C>[O:16]=[C:15]1[CH2:14][CH2:13][CH2:12][S:11][CH:10]1[C:9]([O:8][CH3:7])=[O:19]

Participants

4

Reactant 2

HCID 18379236Methyl 4-[(2-methoxy-2-oxoethyl)sulfanyl]butanoateHCID 23665647Potassium tert-butoxide

Product 1

HCID 18379299Methyl 3-oxotetrahydrothiopyran-2-carboxylateYield 95.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Potassium t-butoxide (1 M in THF) (56.0 mL, 56.0 mmol) was added to an ice cold solution of methyl 4-[(2-methoxy-2-oxoethyl)sulfanyl]butanoate (10.5 g, 50.9 mmol) from (361a), in diethyl ether (200 mL) under nitrogen atmosphere. The reaction was allowed to warm to room temperature and stirred for 2 h. The reaction was partitioned between ethyl ether and water. The organic layer was washed with saturated aqueous sodium bicarbonate, dried over magnesium sulfate and concentrated to give methyl 3-oxotetrahydro-2H-thiopyran-2-carboxylate (8.5 g, 82%) as a yellow oil.

Workup

  1. customThe reaction was partitioned between ethyl ether and water
  2. washThe organic layer was washed with saturated aqueous sodium bicarbonate
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-250d7962f51f4c5d92472ea0460dc772
Source dataset
uspto-grants-2002_12
Patent number
US06495565B2

Reaction notes

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