Diethyl Malonate → 1,3-Diethyl 2-(3-oxocyclohexyl)propanedioate

HRID 523279

反応式

HRID 523279 の反応式
[C:1]1(=[O:7])[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1.[C:8]([O:16][CH2:17][CH3:18])(=[O:15])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11].N12CCCN=C1CCCCC2.CCOC(C)=O>C1COCC1>[O:7]=[C:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:8]([O:16][CH2:17][CH3:18])=[O:15])[CH2:2]1

参加物

6

反応物 4

HCID 7761Diethyl MalonateHCID 8857Ethyl AcetateHCID 135942-Cyclohexen-1-oneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

生成物 1

HCID 3170491,3-Diethyl 2-(3-oxocyclohexyl)propanedioate収率 104%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

A solution of cyclohex-2-enone (3.05 mL, 30 mmol) and diethyl malonate (4.58 mL, 30.0 mmol) in THF (30 mL) was treated with 1,8-diazabicyclo[5.4.0]undec-7-ene (4.52 mL, 30.0 mmol) and heated at 50° C. for 16 h. The cooled mixture was poured into EtOAc and washed sequentially with 1M aqueous HCl and brine. The combined aqueous layers were extracted with EtOAc, and the combined organic phases were dried and concentrated to give diethyl 2-(3-oxocyclohexyl)malonate as an oil (8.0 g), used without further purification. Mass spectrum m/z 257 (M+H)+.

後処理

  1. washwashed sequentially with 1M aqueous HCl and brine
  2. extractionThe combined aqueous layers were extracted with EtOAc
  3. customthe combined organic phases were dried
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-a2ea0672ee5743b9ad4173f2ddb94550
出典データセット
uspto-grants-2016_05
特許番号
US09334290B2

関連ノート

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