Ethyl cyanoformate → Ethyl 4-ethoxy-2-oxocyclohex-3-ene-1-carboxylate

HRID 1917263

反応式

HRID 1917263 の反応式
[Li+].CC([N-]C(C)C)C.[CH2:9]([O:11][C:12]1[CH2:17][CH2:16][CH2:15][C:14](=[O:18])[CH:13]=1)[CH3:10].C([C:21]([O:23][CH2:24][CH3:25])=[O:22])#N>C1COCC1>[CH2:24]([O:23][C:21]([CH:15]1[CH2:16][CH2:17][C:12]([O:11][CH2:9][CH3:10])=[CH:13][C:14]1=[O:18])=[O:22])[CH3:25]

参加物

5

反応物 3

HCID 69336Ethyl cyanoformateHCID 792163-Ethoxycyclohex-2-ene-1-oneHCID 2724682Lithium diisopropylamide

生成物 1

HCID 58997709Ethyl 4-ethoxy-2-oxocyclohex-3-ene-1-carboxylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a −78° C. solution of LDA (192 mmol) in THF (200 mL) was added 3-ethoxy-cyclohex-2-enone (23 mL) dropwise. After stirring for 1 h at −78° C., ethyl cyanoformate (16 mL) was added. The mixture was stirred at −78° C. for 4 h and then was warmed to rt and stirred for 1 h. The mixture was concentrated, diluted with aq. NH4Cl (300 mL), and poured into water. The resulting solids were collected by suction filtration and washed with hexanes followed by water, then was dried and concentrated to provide 17.1 g of a brown solid. TLC (SiO2, 33% EtOAc/hexanes): Rf=0.43.

後処理

  1. stirringThe mixture was stirred at −78° C. for 4 h
  2. temperaturewas warmed to rt
  3. stirringstirred for 1 h
  4. concentrationThe mixture was concentrated
  5. additiondiluted with aq. NH4Cl (300 mL)
  6. additionpoured into water
  7. filtrationThe resulting solids were collected by suction filtration
  8. washwashed with hexanes
  9. customwas dried
  10. concentrationconcentrated

出典と根拠

ORDレコード
ord-bbcc19a53b1445139b5e11a48fa3fafd
出典データセット
uspto-grants-2013_12
特許番号
US08618288B2

関連ノート

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