HCID 69949538、化合物 → 4-CarboxyMethyl-cyclohexanecarboxylic acid ethyl ester

HRID 843677ノート

反応式

HRID 843677 の反応式
[C:1]([O:5][C:6]([CH:8]1[CH2:13][CH2:12][C:11](=[CH:14][C:15]([O:17]C(C)(C)C)=[O:16])[CH2:10][CH2:9]1)=[O:7])(C)(C)[CH3:2].[H][H]>[Pd].C(O)C>[CH2:1]([O:5][C:6]([CH:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]([OH:17])=[O:16])[CH2:10][CH2:9]1)=[O:7])[CH3:2]

参加物

5

反応物 2

HCID 69949538HCID 69949538、化合物HCID 178418361HCID 178418361、化合物

生成物 1

HCID 158961924-CarboxyMethyl-cyclohexanecarboxylic acid ethyl ester収率 99.8%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

A solution of diester (B) (12.5 g, 46.3 mmol) and 10% palladium on activated carbon (5 g) in absolute ethanol (200 mL) was exposed to a hydrogen atmosphere (at balloon pressure) and stirred vigorously for 1 h. After removal of catalyst by filtration and concentration, the resultant colorless oil was dissolved in methylene chloride (150 mL) and TFA (75 mL) and stirred for 15 min. All volatiles were removed by rotary evaporation and the resultant colorless oil placed under high vacuum to give (C) 4-carboxymethyl-cyclohexanecarboxylic acid ethyl ester (9.9 g, 99%) as a white solid. Data for cis/trans mixture: 1H NMR (400 MHz, CD3OD) δ 4.13 (2q, 4 H), 2.58 (m, 1H), 2.30-2.20 (m, 1 H), 2.20 (2d, 4 H), 2.05-1.80 (m, 7 H), 1.80-1.55 (m, 5 H), 1.50-1.38 (m, 3 H), 1.32-1.25 (m, 1 H), 1.25 (2t, 6 H), 1.10-1.00 (m, 2 H); mass spectrum m/z 215 [(M+H)+; calcd for C11H19O4: 215].

後処理

  1. customAfter removal of catalyst
  2. filtrationby filtration and concentration
  3. dissolutionthe resultant colorless oil was dissolved in methylene chloride (150 mL)
  4. stirringTFA (75 mL) and stirred for 15 min
  5. customAll volatiles were removed by rotary evaporation

出典と根拠

ORDレコード
ord-a643fcf0a4834e4c964494dfc7b08432
出典データセット
uspto-grants-2002_04
特許番号
US06380205B1

反応ノート

読み込み中…