Potassium methoxide → Methyl thiane-2-carboxylate

HRID 520425Notes

Reaction equation

HRID 520425 reaction equation
C[O-].[K+].C([S:7][CH:8]([CH2:13][CH2:14][CH2:15][CH2:16]Br)[C:9]([O:11][CH3:12])=[O:10])(=O)C>C1COCC1>[S:7]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:8]1[C:9]([O:11][CH3:12])=[O:10]

Participants

4

Reactant 2

HCID 23664618Potassium methoxideHCID 86690127Methyl 2-(acetylthio)-6-bromohexanoate

Product 1

HCID 57159271Methyl thiane-2-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Neat potassium methoxide (133 mg, 1.893 mmol) was added to a solution of methyl 2-(acetylthio)-6-bromohexanoate (536 mg, 1.893 mmol) in an. THF (18 mL) and the mixture was stirred at rt for 2 days under nitrogen. The crude isolate was purified by silica gel FCC (DCM) to afford methyl tetrahydro-2H-thiopyran-2-carboxylate as a clear oil which was saponified (1N NaOH, MeOH-THF) to afford Cap P-38.

Workup

  1. customThe crude isolate
  2. customwas purified by silica gel FCC (DCM)

Sources & evidence

ORD record
ord-daf36efc5a1d4177bfabaf8b77290dd4
Source dataset
uspto-grants-2016_05
Patent number
US09326973B2

Reaction notes

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