Dimethyl Sulfoxide → 2-(2,5-Difluorophenyl)cyclopropanecarbaldehyde

HRID 1644345노트

반응식

HRID 1644345 반응식
C(Cl)(=O)C(Cl)=O.CS(C)=O.[F:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[CH:19]1[CH2:21][CH:20]1[CH2:22][OH:23].C(N(CC)CC)C>ClCCl>[F:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[CH:19]1[CH2:21][CH:20]1[CH:22]=[O:23]

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 66774368(2-(2,5-Difluorophenyl)cyclopropyl)methanol2회

생성물 1

HCID 866426152-(2,5-Difluorophenyl)cyclopropanecarbaldehyde

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
-78 °C

실험 절차

To a solution of oxalyl chloride (1.2 mL, 13.5 mmol) in dichloromethane at −78° C. was added dimethyl sulfoxide (1.9 mL, 27 mmol) dropwise and it was stirred at −78° C. for 30 minutes. A solution of [2-(2,5-difluorophenyl)cyclopropyl]methanol (Intermediate 69) (830 mg, 4.5 mmol) in dichloromethane was added dropwise. The reaction mixture was stirred at −78° C. for 30 minutes. Triethylamine (6.3 mL, 45 mmol) was added and the reaction mixture was stirred at room temperature for 2 hours. The solvent was removed under reduced pressure. Silica gel chromatography with hexanes/ethyl acetate (9:1) afforded the desired product, 546 mg (66%).

후처리

  1. stirringThe reaction mixture was stirred at −78° C. for 30 minutes
  2. stirringthe reaction mixture was stirred at room temperature for 2 hours
  3. customThe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-375a064717c4493db34111f9c4fa9bdd
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08124602B2

반응 노트

불러오는 중…