Toluene → HCID 54309886, 화합물

HRID 638227노트

반응식

HRID 638227 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

HCID 54309886HCID 54309886, 화합물수율 94%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-7e6f9e401d1241ada707af4ebd3ef4e9
출처 데이터셋
uspto-grants-1985_12
특허 번호
US04560690

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