Water → 1-Acetylsulfanylmethylcyclohexanecarboxylic acid methyl ester

HRID 1160146

Reaction equation

HRID 1160146 reaction equation
[CH3:1][O:2][C:3]([C:5]1([CH2:11]I)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].[C:13]([O-:16])(=[S:15])[CH3:14].[K+].O>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1([CH2:11][S:15][C:13](=[O:16])[CH3:14])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 23670855Potassium ethanethioateHCID 58947958Methyl 1-(iodomethyl)cyclohexanecarboxylate

Product 1

HCID 589479501-Acetylsulfanylmethylcyclohexanecarboxylic acid methyl esterYield 81.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
10 °C

Procedure

To a cold solution of crude 1261-B (109 mmol) in DMF (90 ml) was added Potassium thioacetate (1.2 equiv, 131 mmol, 15 g) maintaining temperature below 30° C. The reaction was stirred for 18 h then cooled to 10° C. and water (160 mL) was added. Reaction was extracted with EtOAc and washed with NaHCO3 sat., then brine. The dark organic layer was dried over MgSO4, filtered and concentrated down to a dark oil. Purification—HPFC (High Pressure Flash Chromatography) 75+M prepacked silica cartridge (1 to 5% EtOAc), UV collection. After concentration, 20.43 g of product 1261-C was obtained.

Workup

  1. temperaturemaintaining temperature below 30° C
  2. customReaction
  3. extractionwas extracted with EtOAc
  4. washwashed with NaHCO3 sat.
  5. dry with materialThe dark organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated down to a dark oil
  8. customPurification—HPFC (High Pressure Flash Chromatography) 75+M prepacked silica cartridge (1 to 5% EtOAc), UV collection
  9. concentrationAfter concentration

Sources & evidence

ORD record
ord-7cd4ff6cd3d54d78a469a9eca91840b5
Source dataset
uspto-grants-2010_10
Patent number
US07816326B2

Linked notes

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