Water → HCID 68847579, compound

HRID 29220Notes

Reaction equation

HRID 29220 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[C:21]([Cl:23])[CH:22]=1)[O:5][CH:6]([CH2:18][CH3:19])[C:7]([NH:9][C:10]([CH3:17])([CH3:16])[C:11]#[C:12][CH2:13]CO)=[O:8].[H-].[Na+].CI.O.CN(C)[CH:31]=[O:32]>CCCCCC.C(OCC)(=O)C>[Cl:23][C:21]1[CH:20]=[C:4]([CH:3]=[C:2]([Cl:1])[CH:22]=1)[O:5][CH:6]([CH2:18][CH3:19])[C:7]([NH:9][C:10]([CH3:16])([CH3:17])[C:11]#[C:12][CH2:13][O:32][CH3:31])=[O:8]

Participants

7

Reactant 5

HCID 962WaterHCID 6228Dimethylformamide3×HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 68849778HCID 68849778, compound

Product 1

HCID 68847579HCID 68847579, compound

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

2-(3,5-Dichlorophenoxy)-N-(1-hydroxymethyl-4-methylpent-2-yn-4-yl)butyramide (prepared as described in Example 2; 1.54 g) in dry N,N-dimethylformamide (20 ml) was added dropwise over 5 minutes to a suspension of sodium hydride (0.28 g, 80% dispersion in mineral oil) in dry N,N-dimethylformamide (2 ml) under an atmosphere of nitrogen at ambient temperature. The mixture was stirred for 2 hours and methyl iodide (0.71 g) in dry N,N-dimethylformamide (5 ml) was added over 1 minute at ambient temperature. The mixture was stirred for 2 hours and stored at ambient temperature for 18 hours. Water was added and the mixture extracted with ethyl acetate (three times). The extracts were combined, washed with water (twice), dried over magnesium sulphate and evaporated under reduced pressure to give a gum that was fractionated by chromatography (silica; hexane/ethyl acetate, 4:1 by volume) to give the required product (0.44 g) as a colourless solid, mp 103-104° C.

Workup

  1. stirringThe mixture was stirred for 2 hours
  2. waitstored at ambient temperature for 18 hours
  3. extractionthe mixture extracted with ethyl acetate (three times)
  4. washwashed with water (twice),
  5. dry with materialdried over magnesium sulphate
  6. customevaporated under reduced pressure
  7. customto give a gum that

Sources & evidence

ORD record
ord-48bd070b7f2945179ac763d19bc1d9ae
Source dataset
uspto-grants-2008_09
Patent number
US07420090B2

Reaction notes

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