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

HRID 29224Notes

Reaction equation

HRID 29224 reaction equation
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]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 10942334Sodium Methoxide2×HCID 21226206Ethyl acetate hexaneHCID 68849646HCID 68849646, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-0e751321a1534d4ea64f59309969889f
Source dataset
uspto-grants-2008_09
Patent number
US07420090B2

Reaction notes

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