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

HRID 393690

Reaction equation

HRID 393690 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+]>CN(C)C=O.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

5

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 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-Iodomethyltetrahydropyran-4-carboxylic acid methyl ester (3.05 g) was dissolved in N,N-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-6b47c1e01b2447308fc8e10bfe12c007
Source dataset
uspto-grants-2004_10
Patent number
US06809100B2

Linked notes

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