Ethyl 2-ethyl-4-oxocyclopent-2-enecarboxylate → Cyclopentanecarboxylic acid, 2-ethyl-4-oxo-, ethyl ester

HRID 1854362ノート

反応式

HRID 1854362 の反応式
[CH2:1]([C:3]1[CH:4]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:5][C:6](=[O:8])[CH:7]=1)[CH3:2]>[Pd].CCOC(C)=O>[CH2:1]([CH:3]1[CH2:7][C:6](=[O:8])[CH2:5][CH:4]1[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH3:2]

参加物

4

反応物 1

HCID 58009992Ethyl 2-ethyl-4-oxocyclopent-2-enecarboxylate

生成物 1

HCID 58010012Cyclopentanecarboxylic acid, 2-ethyl-4-oxo-, ethyl ester収率 99.1%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

A round-bottom flask was charged with 10% palladium on carbon (10 g, 9.4 mmol). The flask was cooled to about 0° C. and EtOAc (400 mL) was added under a nitrogen atmosphere. The cooling bath was removed and ethyl 2-ethyl-4-oxocyclopent-2-enecarboxylate (47.8 g, 263 mmol, Preparation #CC.1) was added. Hydrogen gas was bubbled through the mixture for about 5 min and the mixture was then stirred under a hydrogen atmosphere for about 48 h. The hydrogen source was removed and the mixture was bubbled with nitrogen for about 5 min and was filtered through a pad of Celite®. The filter cake was rinsed with EtOAc (400 mL). The filtrate was concentrated under reduced pressure to give ethyl 2-ethyl-4-oxocyclopentanecarboxylate (about 9:1 mixture cis:trans) (48.0 g, 99%) as a yellow liquid: 1H NMR (CDCl3) δ 4.23-4.10 (m, 2H), 3.22 (m, 1H), 2.59-2.50 (m, 1H), 2.44-2.28 (m, 3H), 2.26-2.16 (m, 1H), 1.58-1.46 (m, 1H), 1.41-1.30 (m, 1H), 1.30-1.23 (m, 3H), 1.02-0.91 (m, 3H).

後処理

  1. customThe cooling bath was removed
  2. customHydrogen gas was bubbled through the mixture for about 5 min
  3. customThe hydrogen source was removed
  4. customthe mixture was bubbled with nitrogen for about 5 min
  5. filtrationwas filtered through a pad of Celite®
  6. washThe filter cake was rinsed with EtOAc (400 mL)
  7. concentrationThe filtrate was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-f638ec1aa8444ce99d4c4aa4f5608458
出典データセット
uspto-grants-2015_02
特許番号
US08962629B2

反応ノート

読み込み中…