Ethylene Glycol → Ethyl 1-methoxycarbonyl-3-oxopiperidine-4-carboxylate ethylene acetal

HRID 1277630노트

반응식

HRID 1277630 반응식
[CH3:1][O:2][C:3]([N:5]1[CH2:10][CH2:9][CH:8]([C:11]([O:13][CH2:14][CH3:15])=O)[C:7](=[O:16])[CH2:6]1)=[O:4].[CH2:17]([OH:20])[CH2:18][OH:19].C1(C)C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>C(OCC)(=O)C.C(Cl)Cl.O>[CH2:17]1[O:20][C:11]([CH:8]2[CH2:9][CH2:10][N:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6][C:7]2=[O:16])([O:13][CH2:14][CH3:15])[O:19][CH2:18]1

참가 물질

8

반응물 4

HCID 174Ethylene GlycolHCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 105613714-Ethyl 1-methyl 3-oxopiperidine-1,4-dicarboxylate

생성물 1

HCID 70082215Ethyl 1-methoxycarbonyl-3-oxopiperidine-4-carboxylate ethylene acetal

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of ethyl 1-methoxycarbonyl-3-oxopiperidine-4-carboxylate (9.0 g; 39 mmol), ethylene glycol (100 ml), 4-toluenesulfonic acid (0.7 g), and benzene (500 ml) was refluxed for 6 days using a Dean-Stark water separator. The mixture was washed with aqueous sodium carbonate (300 ml; 1 M), water (300 ml), and saturated aqueous sodium chloride (300 ml). The organic phase was dried (K2CO3) and evaporated in vacuo to give 8.6 of an oil. CC [silica gel (Woelm 0.063-0.1 mm): 350 g; eluents: methylene chloride to which ethyl acetate (20-35%) was added] followed by ball-tube distillation at 40 Pa (oven temperature 170° C.) gave VIIIa (7.0 g; 65%) as a colourless oil. IR (film): 2970 (s), 2900 (s), 1730 (s) cm-1. 1H NMR (CCl4): δ4.05 (q, J 7 Hz) and 3.92 (s) (a total of 6H), 3.60 (s) and 3.7-3.0 (m) (a total of 7H), 2.8-2.5 (1H, t), 2.2-1.6 (2H, m), 1.23 (3H, t, J 7 Hz).

후처리

  1. temperaturewas refluxed for 6 days
  2. washThe mixture was washed with aqueous sodium carbonate (300 ml; 1 M), water (300 ml), and saturated aqueous sodium chloride (300 ml)
  3. dry with materialThe organic phase was dried (K2CO3)
  4. customevaporated in vacuo
  5. customto give 8.6 of an oil
  6. customfollowed by ball-tube
  7. distillationdistillation at 40 Pa (oven temperature 170° C.)
  8. customgave VIIIa (7.0 g; 65%) as a colourless oil

출처 및 근거

ORD 기록
ord-c770ce4d92344889aecaa4794dfd3ee7
출처 데이터셋
uspto-grants-1981_07
특허 번호
US04278676

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