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

HRID 29224ノート

反応式

HRID 29224 の反応式
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]

参加物

7

反応物 4

HCID 5238Sodium IodideHCID 10942334Sodium Methoxide2 回HCID 21226206Ethyl acetate hexaneHCID 68849646HCID 68849646、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-0e751321a1534d4ea64f59309969889f
出典データセット
uspto-grants-2008_09
特許番号
US07420090B2

反応ノート

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