Acetonitrile → Ethyl 4-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)benzoate

HRID 1382850노트

반응식

HRID 1382850 반응식
F[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[O:13]1[C:17]2([CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[O:16][CH2:15][CH2:14]1.C([O-])([O-])=O.[K+].[K+].C(#N)C>O.CCOCC>[CH2:9]([O:8][C:6](=[O:7])[C:5]1[CH:11]=[CH:12][C:2]([N:20]2[CH2:21][CH2:22][C:17]3([O:16][CH2:15][CH2:14][O:13]3)[CH2:18][CH2:19]2)=[CH:3][CH:4]=1)[CH3:10]

참가 물질

7

반응물 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 67976Benzoic acid, 4-fluoro-, ethyl ester

생성물 1

HCID 12717439Ethyl 4-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)benzoate수율 30.5%

시약·촉매·용매 2

HCID 962Water용매HCID 3283Diethyl Ether용매

실험 절차

A mixture of 50 g (0.349 mol) of ethyl p-fluorobenzoate, 185 g (1.29 mol) of 1,4-dioxa-8-azaspiro[4.5]decane, 73 g (0.5282 mol) of K2CO3, and 400 ml of acetonitrile is stirred at 90°-100° C. for three days. The reaction mixture is allowed to cool to ambient temperature, diluted with water, and extracted with methylene chloride. The combined organic extracts are washed with brine, dried over Na2SO4, and concentrated in vacuo to give a pasty solid. Trituration with ether furnishes 31 g (23%) of title compound: IR (KBr) 1695 and 1610 cm-1 ; NMR (CDCl3) δ7.98 (d, 2H), 6.96 (m, 2H), 4.36 (q, 2H), 4.02 (s, 4H), 3.58-3.48 (m, 4H), 1.92-1.80 (m, 4H), and 1.38 (t, 3H).

후처리

  1. extractionextracted with methylene chloride
  2. washThe combined organic extracts are washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customto give a pasty solid

출처 및 근거

ORD 기록
ord-6b8a15b6b42e438e8dcfeb14585ca7ed
출처 데이터셋
uspto-grants-1989_02
특허 번호
US04808612

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