Diethyl Oxalate → Ethyl 4-(4-chlorophenyl)-3-methyl-2,4-dioxobutanoate

HRID 1510429ノート

反応式

HRID 1510429 の反応式
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].O1CCCC1.[CH3:16][CH2:17][C:18]([C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1)=[O:19].[C:27]([O:34][CH2:35][CH3:36])(=[O:33])[C:28]([O:30]CC)=O>C(OCC)C>[Cl:26][C:23]1[CH:22]=[CH:21][C:20]([C:18](=[O:19])[CH:17]([CH3:16])[C:28](=[O:30])[C:27]([O:34][CH2:35][CH3:36])=[O:33])=[CH:25][CH:24]=1

参加物

6

反応物 4

HCID 7268Diethyl OxalateHCID 8028TetrahydrofuranHCID 226974'-ChloropropiophenoneHCID 2733832Lithium Hexamethyldisilazide

生成物 1

HCID 5051380Ethyl 4-(4-chlorophenyl)-3-methyl-2,4-dioxobutanoate収率 33.7%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

反応条件

温度
-78 °C

実験手順

A 1.0 M solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran (30 mL, 30 mmol) in anhydrous diethyl ether (120 mL) under argon was cooled to −78° C. in a dry ice/acetone bath. A solution of 4-chloropropiophenone (5.0 g, 29.7 mmol) in anhydrous ether (24 mL) was added dropwise and the mixture was stirred an additional 45 minutes at −78° C. Diethyl oxalate (4.6 mL, 33.9 mmol) was added in one portion; the reaction was warmed to room temperature, and stirred overnight. The light yellow precipitate that formed was collected, washed with ether and dried under vacuum to obtain the lithium enolate of ethyl 4-(4-chlorophenyl)-3-methyl-2,4-dioxobutanoate (2.75 g, 10.0 mmol).

後処理

  1. temperaturethe reaction was warmed to room temperature
  2. stirringstirred overnight
  3. customThe light yellow precipitate that formed
  4. customwas collected
  5. washwashed with ether
  6. customdried under vacuum

出典と根拠

ORDレコード
ord-3b5cd30040154919a6e1f47720c82fe2
出典データセット
uspto-grants-2012_07
特許番号
US08211927B2

反応ノート

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