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

HRID 47358노트

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HRID 47358 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

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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. stirringThe reaction mixture is stirred for 6 hours at −75° C
  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-76382879dc454d6b9324a56b45a98434
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06699876B2

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