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

HRID 1635073ノート

反応式

HRID 1635073 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
-75 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-f1bc394fdec64440979fd9414b8cd82e
出典データセット
uspto-grants-2003_01
特許番号
US06509345B2

反応ノート

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