Sodium Iodide → 2-(3,5-dichlorophenoxy)-N-(1-methoxy-6-methylhept-4-yn-6-yl) butyramide

HRID 29224노트

반응식

HRID 29224 반응식
C[O-].[Na+].[Cl:4][C:5]1[CH:6]=[C:7]([CH:24]=[C:25]([Cl:27])[CH:26]=1)[O:8][CH:9]([CH2:22][CH3:23])[C:10]([NH:12][C:13]([CH3:21])([CH3:20])[C:14]#[C:15][CH2:16][CH2:17][CH2:18]Cl)=[O:11].[I-].[Na+].CCCCCC.[C:36](OCC)(=[O:38])C>CO.O>[Cl:4][C:5]1[CH:6]=[C:7]([CH:24]=[C:25]([Cl:27])[CH:26]=1)[O:8][CH:9]([CH2:22][CH3:23])[C:10]([NH:12][C:13]([CH3:21])([CH3:20])[C:14]#[C:15][CH2:16][CH2:17][CH2:18][O:38][CH3:36])=[O:11]

참가 물질

7

반응물 4

HCID 5238Sodium IodideHCID 10942334Sodium Methoxide2회HCID 21226206Ethyl acetate hexaneHCID 68849646HCID 68849646, 화합물

생성물 1

HCID 115238832-(3,5-dichlorophenoxy)-N-(1-methoxy-6-methylhept-4-yn-6-yl) butyramide

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

To a stirred solution of sodium methoxide (prepared from sodium, 0.014 g) in methanol (2 ml) at ambient temperature was added 2-(3,5-dichlorophenoxy)-N-(1-chloro-6-methylhept-4-yn-6-yl) butyramide (0.20 g) followed by further sodium methoxide (0.3 g) and sodium iodide (0.1 g). The mixture was stirred at ambient temperature under an atmosphere of nitrogen for 4 hours, heated to reflux for a total of 10 hours, cooled to ambient temperature then stored for 18 hours. The reaction mixture was diluted with water, extracted with ethyl acetate (three times) and the extracts were combined, washed with brine then evaporated under reduced pressure to give a yellow oil. The oil was fractionated by chromatography (silica; hexane/ethyl acetate, 3:1 by volume) to give the required product as a colourless oil, 0.055 g, 1H NMR (CDCl3) δ: 0.98-1.04(3H, t); 1.60(6H, s); 1.72-1.78(2H, m); 1.92-2.00(2H, m); 2.24-2.28((2H, t); 3.34(3H, s); 3.42-3.46(2H, t); 4.36-4.38(1H, t); 6.28(1H, s); 6.84(2H, s); 7.02(1H, s).

후처리

  1. temperatureheated
  2. temperatureto reflux for a total of 10 hours
  3. temperaturecooled to ambient temperature
  4. waitthen stored for 18 hours
  5. extractionextracted with ethyl acetate (three times)
  6. washwashed with brine
  7. customthen evaporated under reduced pressure
  8. customto give a yellow oil

출처 및 근거

ORD 기록
ord-0e751321a1534d4ea64f59309969889f
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07420090B2

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