4-Iodomethyl-tetrahydro-pyran-4-carboxylic acid methyl ester → Methyl 4-[(acetylsulfanyl)methyl]oxane-4-carboxylate

HRID 1005842Notes

Reaction equation

HRID 1005842 reaction equation
[CH3:1][O:2][C:3]([C:5]1([CH2:11]I)[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)=[O:4].[C:13]([O-:16])(=[S:15])[CH3:14].[K+]>O>[CH3:1][O:2][C:3]([C:5]1([CH2:11][S:15][C:13](=[O:16])[CH3:14])[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)=[O:4]

Participants

4

Reactant 2

HCID 227197884-Iodomethyl-tetrahydro-pyran-4-carboxylic acid methyl esterHCID 23670855Potassium ethanethioate

Product 1

HCID 23448262Methyl 4-[(acetylsulfanyl)methyl]oxane-4-carboxylateYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Iodomethyltetrahydropyran-4-carboxylic acid methyl ester (3.05 g) was dissolved in NN-dimethylformamide (20 ml) at room temperature and potassium thioacetate (1.47 g) added. The mixture was stirred for 18 hours then diluted with water (50 ml) and extracted with diethyl ether (4×25 ml). The combined organics were washed with saturated sodium bicarbonate solution (3×20 ml) and brine (20 ml), then dried (MgSO4), filtered and evaporated under reduced pressure to give the title compound as a yellow solid (2.42 g, 97%).

Workup

  1. extractionextracted with diethyl ether (4×25 ml)
  2. washThe combined organics were washed with saturated sodium bicarbonate solution (3×20 ml) and brine (20 ml)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-7e309e5c46524199be8d29f2cbe6f870
Source dataset
uspto-grants-2004_09
Patent number
US06787536B2

Reaction notes

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