2-Ketobutyric acid methyl ester → Methyl 2-(2-fluoro-3-methyl-4-pyridinyl)-2-hydroxybutanoate

HRID 47355

反応式

HRID 47355 の反応式
C([Li])CCC.[F:6][C:7]1[C:12]([CH3:13])=[C:11](I)[CH:10]=[CH:9][N:8]=1.[O:15]=[C:16]([CH2:21][CH3:22])[C:17]([O:19][CH3:20])=[O:18].O.C1COCC1>CCCCCC.C1COCC1>[F:6][C:7]1[C:12]([CH3:13])=[C:11]([C:16]([OH:15])([CH2:21][CH3:22])[C:17]([O:19][CH3:20])=[O:18])[CH:10]=[CH:9][N:8]=1

参加物

7

反応物 4

HCID 5451272-Ketobutyric acid methyl esterHCID 117762982-Fluoro-4-iodo-3-methylpyridineHCID 21881883Oxolane--water (1/1)HCID 178418339Butyllithium

生成物 1

HCID 22745020Methyl 2-(2-fluoro-3-methyl-4-pyridinyl)-2-hydroxybutanoate

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
-78 °C

実験手順

6.9 ml (11 mmol) of 1.6M butyllithium in hexane are added dropwise to a solution, stirred at −78° C. of 2.6 g (11 mmol) of 2-fluoro-4-iodo-3-methylpyridine (described in J.O.C., 1993, 58, pp. 7832) in 100 ml of THF. The reaction mixture is then stirred for 10 minutes at −78° C. before the addition of a solution of 1.5 g (12.9 mmol) of methyl 2-oxo-butyrate in 20 ml of THF. The reaction mixture is stirred for 10 minutes at −78° C., and then hydrolysed with a mixture of water/THF. The aqueous phase is decanted and then extracted 3 times with 50 ml of methyl acetate each time. The combined organic phases are dried, concentrated and purified by chromatography over silica (eluant dichloromethane/acetone 95/5) to yield the expected product.

後処理

  1. customThe aqueous phase is decanted
  2. extractionextracted 3 times with 50 ml of methyl acetate each time
  3. customThe combined organic phases are dried
  4. concentrationconcentrated
  5. custompurified by chromatography over silica (eluant dichloromethane/acetone 95/5)

出典と根拠

ORDレコード
ord-c3e61e1cf6d644b09d152747e13243a8
出典データセット
uspto-grants-2004_03
特許番号
US06699876B2

関連ノート

読み込み中…