Toluene → HCID 54309886、化合物

HRID 638227ノート

反応式

HRID 638227 の反応式
C(O[CH:4](OCC)[C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH3:13])=[CH:7][CH:6]=1)C.[C:17]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])#[N:18].C([O-])(=O)C.[NH4+].C1(C)C=CC=CC=1>O>[C:17]([C:19](=[CH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH3:13])=[CH:7][CH:6]=1)[C:20]([O:22][CH2:23][CH3:24])=[O:21])#[N:18]

参加物

6

反応物 4

HCID 1140TolueneHCID 7764Ethyl cyanoacetateHCID 517165Ammonium AcetateHCID 6009134-Propylbenzaldehyde diethyl acetal

生成物 1

HCID 54309886HCID 54309886、化合物収率 94%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of 20.0 g (90 mmole) 4-n-propylbenzaldehyde diethylacetal, 20.4 g (180 mmole) ethyl cyanoacetate, 7.2 g (93.4 mmole) ammonium acetate and 60 ml toluene are heated at reflux for six hours, cooled and poured into water. The resulting mixture was extracted with ethyl ether, dried (MgSO4) and the volatiles evaporated in vacuo to afford 23.0 g crude yellow oil which was purified by chromatography on a silica gel column, eluting with 2:1 methylene chloride/hexane to give 20.58 g (94%) of the desired product. 1H-NMR(CDCl3)ppm(delta): 0.85-1.95 (m, 8H), 2.45-2.70 (t, 2H), 4.15-4.60 (q, 2H), 7.15-8.05 (q, 4H), 8.25 (s, 1H).

後処理

  1. temperatureare heated
  2. temperatureat reflux for six hours
  3. temperaturecooled
  4. extractionThe resulting mixture was extracted with ethyl ether
  5. dry with materialdried (MgSO4)
  6. customthe volatiles evaporated in vacuo
  7. customto afford 23.0 g crude yellow oil which
  8. customwas purified by chromatography on a silica gel column
  9. washeluting with 2:1 methylene chloride/hexane

出典と根拠

ORDレコード
ord-7e6f9e401d1241ada707af4ebd3ef4e9
出典データセット
uspto-grants-1985_12
特許番号
US04560690

反応ノート

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