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

HRID 1879244ノート

反応式

HRID 1879244 の反応式
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]

参加物

6

反応物 3

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

生成物 1

HCID 46703846N-methoxy-N-methylhept-6-enamide収率 97%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-3793365b54694eabbd614a7081c47ada
出典データセット
uspto-grants-2012_11
特許番号
US08314062B2

反応ノート

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