2-Dimethylaminopyridine → 2,2-Difluoro-5-methoxyvaleronitrile

HRID 568982

반응식

HRID 568982 반응식
S(Cl)(Cl)=O.CN(C1C=CC=CN=1)C.[F:14][C:15]([F:24])([CH2:19][CH2:20][CH2:21][O:22][CH3:23])[CH:16]=[N:17]O.CC1C=CN=C(N)C=1C>ClCCl>[F:14][C:15]([F:24])([CH2:19][CH2:20][CH2:21][O:22][CH3:23])[C:16]#[N:17]

참가 물질

6

반응물 4

HCID 218852-DimethylaminopyridineHCID 24386Thionyl ChlorideHCID 110078842-Amino-3,4-dimethylpyridineHCID 736640532,2-Difluoro-5-methoxy-1-pentanal oxime

생성물 1

HCID 140976002,2-Difluoro-5-methoxyvaleronitrile수율 67.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

반응 조건

온도
-15 °C

실험 절차

Thionyl chloride (809 mg, 6.8 mmoles) in ice cold dry dichloromethane (7 ml) is added to a solution of dimethylamino pyridine (903 mg, 7.4 mmoles) in dichloromethane (15 ml) kept under nitrogen and cooled at -15° C. The oxime 34 (1.04 g, 6.2 mmoles), dissolved in dichloromethane (20 ml) is added, followed by addition of dimethyl aminopyridine as a solid (903 mg, 7.4 mmoles). The reaction mixture is then allowed to rise to room temperature, kept at 25° C. for 1 hour, diluted with dichloromethane, washed with 1N HCl, and finally with water. Concentration of the organic phase, previously dried over sodium sulfate, (30° C., 100 mm Hg) affords the title compound (620 mg) which is purified by bulb to bulb distillation (50° C., 30 mm Hg): 485 mg (52%).

후처리

  1. additionis added
  2. customto rise to room temperature
  3. washwashed with 1N HCl
  4. dry with materialConcentration of the organic phase, previously dried over sodium sulfate, (30° C., 100 mm Hg)

출처 및 근거

ORD 기록
ord-9af99a4085184e959ef37b2a1fab5840
출처 데이터셋
uspto-grants-1988_03
특허 번호
US04730006

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