Ethyl Acetate → (E)-3-(4-Iodo-phenyl)-2-methyl-acrylic acid ethyl ester

HRID 1765700ノート

反応式

HRID 1765700 の反応式
C([C:3](CC)(CC)[CH:4](P(O)(O)=O)[C:5]([O-:7])=[O:6])C.[CH2:16]([Li])[CH2:17]CC.[I:21][C:22]1[CH:29]=[CH:28][C:25]([CH:26]=O)=[CH:24][CH:23]=1.C(OCC)(=O)C>O1CCCC1.CCCCCC>[CH2:16]([O:7][C:5](=[O:6])/[C:4](/[CH3:3])=[CH:26]/[C:25]1[CH:28]=[CH:29][C:22]([I:21])=[CH:23][CH:24]=1)[CH3:17]

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 966574-IodobenzaldehydeHCID 92003523Triethyl-2-phosphonopropionateHCID 178418339Butyllithium

生成物 1

HCID 57424206(E)-3-(4-Iodo-phenyl)-2-methyl-acrylic acid ethyl ester収率 99%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

実験手順

A stirred, cooled (−78° C.) solution of triethyl-2-phosphonopropionate (10 g, 41.9 mmol) in anhydrous tetrahydrofuran (100 mL) was treated with a 1.6M solution of n-butyl lithium in hexanes (25 mL, 40 mmol). After 10 min, the reaction mixture was cannulated into a cooled (−78° C.) solution of 4-iodo-benzaldehyde (4.66 g, 20 mmol) in tetrahydrofuran (25 mL). After 30 minutes, 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 9–10% ethyl acetate in hexane as the eluent to afford the title compound (6.3 g, 99%).

後処理

  1. waitAfter 30 minutes
  2. customit was quenched with saturated aqueous ammonium chloride solution
  3. extractionextracted with diethyl ether (×2)
  4. dry with materialThe combined organic phase was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto afford an oil that

出典と根拠

ORDレコード
ord-593d708ceb45495cbc3fefd14ff79672
出典データセット
uspto-grants-2007_06
特許番号
US07226951B2

反応ノート

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