Diethylamine → 5-Methyl-2-oxo-cyclohexanecarboxylic acid diethylamide

HRID 1506715ノート

反応式

HRID 1506715 の反応式
C(O[C:4]([CH:6]1[CH2:11][CH:10]([CH3:12])[CH2:9][CH2:8][C:7]1=[O:13])=[O:5])C.[CH2:14]([NH:16][CH2:17][CH3:18])[CH3:15]>CN(C1C=CN=CC=1)C.C1(C)C=CC=CC=1>[CH2:14]([N:16]([CH2:17][CH3:18])[C:4]([CH:6]1[CH2:11][CH:10]([CH3:12])[CH2:9][CH2:8][C:7]1=[O:13])=[O:5])[CH3:15]

参加物

5

反応物 2

HCID 8021DiethylamineHCID 458119Ethyl 5-methyl-2-oxocyclohexane-1-carboxylate

生成物 1

HCID 666798285-Methyl-2-oxo-cyclohexanecarboxylic acid diethylamide収率 65.1%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 1140Toluene溶媒

実験手順

5-Methyl-2-oxo-cyclohexanecarboxylic acid ethyl ester (45) (5.9 g, 32 mmol), DMAP (1.12 g, 10 mmol) and diethylamine (4.7 g, 65 mmol, 6.7 mL) in toluene (90 mL) were heated at reflux for 4 days. The reaction was allowed to cool and the toluene was removed under reduced pressure to give a yellow oil. The crude material was purified by silica gel chromatography eluting with petrol (A) and ethyl acetate (B) (20-50% B, 80 g) to afford 4.4 g (65%) of 5-methyl-2-oxo-cyclohexanecarboxylic acid diethylamide (46) as a yellow oil. The structure was confirmed 1H NMR (300 MHz, CDCl3) δH 0.8-1.05 (9H, m, CH3 and N(CH2CH3)2), 1.05-2.10 (5H, m, 5-CH and 4- and 6-CH2), 2.15-2.80 (2H, m, 3-CH2), 2.95-3.55 (5H, m, 1-CH and N(CH2CH3)2).

後処理

  1. temperatureat reflux for 4 days
  2. temperatureto cool
  3. customthe toluene was removed under reduced pressure
  4. customto give a yellow oil
  5. customThe crude material was purified by silica gel chromatography
  6. washeluting with petrol (A) and ethyl acetate (B) (20-50% B, 80 g)

出典と根拠

ORDレコード
ord-a18cf294a02044b5872d086136027258
出典データセット
uspto-grants-2015_12
特許番号
US09220795B2

反応ノート

読み込み中…