Water → 3-(3-Allyl-2-fluoro-4-pyridinyl)-3-pentanol

HRID 1635073노트

반응식

HRID 1635073 반응식
C([Li])CCC.[CH2:6]([C:9]1[C:10]([F:16])=[N:11][CH:12]=[CH:13][C:14]=1I)[CH:7]=[CH2:8].[CH3:17][CH2:18][C:19](=[O:22])[CH2:20][CH3:21].O>CCCCCC.C1COCC1>[CH2:6]([C:9]1[C:10]([F:16])=[N:11][CH:12]=[CH:13][C:14]=1[C:19]([OH:22])([CH2:20][CH3:21])[CH2:18][CH3:17])[CH:7]=[CH2:8]

참가 물질

7

반응물 4

HCID 962WaterHCID 7288Ethyl ketoneHCID 227450382-Fluoro-4-iodo-3-(prop-2-en-1-yl)pyridineHCID 178418339Butyllithium

생성물 1

HCID 227450133-(3-Allyl-2-fluoro-4-pyridinyl)-3-pentanol

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

반응 조건

온도
-75 °C

실험 절차

27 ml (43.3 mmol) of 1.6M butyllithium in hexane are added, at −75° C., to a solution of 11.4 g (43.3 mmol) of 3-allyl-2-fluoro-4-iodopyridine (prepared according to the process described in J.O.C., 1993, 58, pp.7832) in 250 ml of THF. After 30 minutes' stirring at −75° C. a solution of 4.6 ml of 3-pentanone in 100 ml of THF is added dropwise. The reaction mixture is stirred for 6 hours at −75° C. After returning to room temperature, the mixture is hydrolysed with 100 ml of water and extracted with ethyl acetate. The organic phase is dried, concentrated and purified by chromatography over silica (eluant:cyclohexane/ethyl acetate 8/2) to yield the expected product.

후처리

  1. customprepared
  2. additionis added dropwise
  3. customAfter returning to room temperature
  4. extractionextracted with ethyl acetate
  5. customThe organic phase is dried
  6. concentrationconcentrated
  7. custompurified by chromatography over silica (eluant:cyclohexane/ethyl acetate 8/2)

출처 및 근거

ORD 기록
ord-f1bc394fdec64440979fd9414b8cd82e
출처 데이터셋
uspto-grants-2003_01
특허 번호
US06509345B2

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