Tetrahydrofuran → 2-Propenoic acid, 3-(3-iodophenyl)-, ethyl ester

HRID 1765699

反応式

HRID 1765699 の反応式
C([Li])CCC.[I:6][C:7]1[CH:14]=C[C:10](C=O)=[CH:9][CH:8]=1.[C:15](OCC)(=[O:17])[CH3:16].[O:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1>CCCCCC>[CH2:15]([O:17][C:25](=[O:21])[CH:24]=[CH:23][C:22]1[CH:10]=[CH:9][CH:8]=[C:7]([I:6])[CH:14]=1)[CH3:16]

参加物

6

反応物 4

HCID 8028Tetrahydrofuran2 回HCID 8857Ethyl AcetateHCID 966574-IodobenzaldehydeHCID 178418339Butyllithium

生成物 1

HCID 545009022-Propenoic acid, 3-(3-iodophenyl)-, ethyl ester収率 95%

試薬・触媒・溶媒 1

HCID 8058Hexane溶媒

反応条件

温度
0 °C

実験手順

A stirred, cooled (−78° C.) solution of triethylphosphonoacetate (11.44 g, 51 mmol) in anhydrous tetrahydrofuran (100 mL) was treated with a 1.6M solution of n-butyl lithium in hexanes (30 mL, 48 mmol). After 10 min, the reaction mixture was cannulated into a cooled (−78° C.) solution of 4-iodo-benzaldehyde (3.7 g, 16 mmol) in tetrahydrofuran (20 mL). The reaction mixture was allowed to warm to 0° C. over 1 h. It was quenched with saturated aqueous ammonium chloride solution and extracted with diethyl ether (×2). The combined organic phase was dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford an oil that was subjected to flash column chromatography over silica gel (230–400 mesh) using 8–10% ethyl acetate in hexane as the eluent to afford the title compound (4.6 g, 95%).

後処理

  1. customIt was quenched with saturated aqueous ammonium chloride solution
  2. extractionextracted with diethyl ether (×2)
  3. dry with materialThe combined organic phase was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto afford an oil that

出典と根拠

ORDレコード
ord-d0c6965d8e554527a16f5a6d9e1bacd8
出典データセット
uspto-grants-2007_06
特許番号
US07226951B2

関連ノート

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