1,2-Dichloroethane → N-methoxy-N-methylhept-6-enamide

HRID 1879244노트

반응식

HRID 1879244 반응식
C(Cl)CCl.[C:5]([OH:13])(=O)[CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11].[Cl-].[CH3:15][O:16][NH2+:17][CH3:18]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:15][O:16][N:17]([CH3:18])[C:5](=[O:13])[CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11]

참가 물질

6

반응물 3

HCID 111,2-DichloroethaneHCID 707056-Heptenoic acidHCID 11040634Methoxy(methyl)azanium;chloride

생성물 1

HCID 46703846N-methoxy-N-methylhept-6-enamide수율 97%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

실험 절차

EDC (1.1 eq.) was added in small portions over 1.5 h to a stirred mixture of hept-6-enoic acid, methoxy(methyl)ammonium chloride (1.1 eq.) and DMAP (1.1 eq.) in CH2Cl2 (0.2 M). After 14 h, the mixture was diluted with CH2Cl2, then washed sequentially with hydrochloric acid (1 M), NaOH (1M), brine and dried (Na2SO4). Evaporation of the solvent afforded the title compound (97%) as a colorless oil. 1H NMR (400 MHz, CDCl3, 300 K) δ 5.87-5.75 (m, 1H), 5.01 (d, J 17.1, 1H), 4.95 (d, J 10.1, 1H), 3.68 (s, 3H), 3.18 (s, 3H), 2.48-2.36 (m, 2H), 2.13-2.04 (m, 2H), 1.71-1.60 (m, 2H), 1.50-1.40 (m, 2H).

후처리

  1. washwashed sequentially with hydrochloric acid (1 M), NaOH (1M), brine
  2. dry with materialdried (Na2SO4)
  3. customEvaporation of the solvent

출처 및 근거

ORD 기록
ord-3793365b54694eabbd614a7081c47ada
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08314062B2

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