Water → 1-Acetylsulfanylmethylcyclohexanecarboxylic acid methyl ester

HRID 1160146

반응식

HRID 1160146 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 589479501-Acetylsulfanylmethylcyclohexanecarboxylic acid methyl ester수율 81.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
10 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7cd4ff6cd3d54d78a469a9eca91840b5
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07816326B2

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