Diethyl Ether → Methyl 4-[(acetylsulfanyl)methyl]oxane-4-carboxylate

HRID 1840506Notes

Reaction equation

HRID 1840506 reaction equation
[O:1]([CH2:8][CH2:9][CH2:10][S:11][C:12](=[O:14])[CH3:13])[C:2]1C=CC=CC=1.C([O-:18])(=S)C.[K+].C(=O)(O)[O-].[Na+].[CH3:25][CH2:26][O:27][CH2:28][CH3:29]>CN(C=O)C>[C:12]([S:11][CH2:10][C:9]1([C:8]([O:1][CH3:2])=[O:18])[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1)(=[O:14])[CH3:13]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 516892Sodium BicarbonateHCID 11218066HCID 11218066, compoundHCID 23670855Potassium ethanethioate

Product 1

HCID 23448262Methyl 4-[(acetylsulfanyl)methyl]oxane-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of Intermediate 4 (3.05 g) in DMF (20 ml) was treated with potassium thioacetate (1.47 g) at room temperature for 18 h, then the brown solution was added to 5% sodium bicarbonate solution and extacted with ether (3×200 ml). The solvent was washed with water (200 ml) and brine, dried over MgSO4 and evaporated to give the title compound (2.42 g) as a white solid.

Workup

  1. washThe solvent was washed with water (200 ml) and brine
  2. dry with materialdried over MgSO4
  3. customevaporated

Sources & evidence

ORD record
ord-4475738076194ffeb83194fcf1cfd083
Source dataset
uspto-grants-2004_01
Patent number
US06680338B2

Reaction notes

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