Dimethyl Sulfoxide → 2-(4-Fluorophenyl)cyclohexan-1-one

HRID 1023469노트

반응식

HRID 1023469 반응식
C(Cl)(=O)C(Cl)=O.CS(C)=O.[F:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]2[OH:24])=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl>[F:11][C:12]1[CH:13]=[CH:14][C:15]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][C:19]2=[O:24])=[CH:16][CH:17]=1

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 20487437HCID 20487437, 화합물

생성물 1

HCID 130895402-(4-Fluorophenyl)cyclohexan-1-one수율 69.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

반응 조건

온도
-78 °C

실험 절차

To a solution of oxalyl chloride (0.45 mL, 5.2 mmol) in dry dichloromethane (15 mL) at −78° C. is added a solution of DMSO (0.73 mL, 10.3 mmol) in dichloromethane (10 mL) dropwise, and the resulting mixture is allowed to stir at −78° C. for 30 minutes. Then a solution of 2-(4-Fluoro-phenyl)-cyclohexanol (500 mg, 2.57 mmol) in dichloromethane (5 mL) is added and stirred for 15 minutes. Then triethylamine (2.87 mL, 15.4 mmol) is added and the reaction is allowed to slowly warm up to 20° C. and stirred for 16 hours. The mixture is poured into ice-water (30 mL) and organic layer is washed with water (10 mL×5), then brine (10 mL×1) and dried over anhdrous sodium sulfate. After concentration, the crude is purified by silica flash column chromatography using EtOAc in Heptane (gradient from 0% to 30%) to give 342 mg of the desired product.

후처리

  1. stirringstirred for 15 minutes
  2. temperatureto slowly warm up to 20° C.
  3. stirringstirred for 16 hours
  4. washis washed with water (10 mL×5)
  5. dry with materialbrine (10 mL×1) and dried over anhdrous sodium sulfate
  6. concentrationAfter concentration
  7. customthe crude is purified by silica flash column chromatography

출처 및 근거

ORD 기록
ord-c512da44ff1a4f44953c783a1409dfd6
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722709B2

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