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

HRID 1869826

反応式

HRID 1869826 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-c9a0d35d5a4f4dc08a415ae92c790b67
出典データセット
uspto-grants-2009_12
特許番号
US07638648B2

関連ノート

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