Sodium hydride → Ethyl 2-(4-n-Propylphenylthio)nonanoate

HRID 2379596Notes

Reaction equation

HRID 2379596 reaction equation
[H-].[Na+].[CH2:3]([C:6]1[CH:11]=[CH:10][C:9]([SH:12])=[CH:8][CH:7]=1)[CH2:4][CH3:5].Br[CH:14]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:15]([O:17][CH2:18][CH3:19])=[O:16]>CN(C)C=O.C(OCC)(=O)C>[CH2:3]([C:6]1[CH:11]=[CH:10][C:9]([S:12][CH:14]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:8][CH:7]=1)[CH2:4][CH3:5]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 110997Ethyl 2-bromononan-1-oateHCID 27604894-n-Propylthiophenol

Product 1

HCID 14995384Ethyl 2-(4-n-Propylphenylthio)nonanoateYield 81%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.6 g (0.033 mole) sodium hydride (50% dispersion in mineral oil) was added to a solution of 5.0 g (0.033 mole) 4-propylthiophenol in 25 ml anhydrous dimethylformamide. After 15 minutes, 8.8 g (0.033 mole) ethyl 2-bromononanoate (prepared according to J. Labelled Compounds Radiopharm. 14, 713 (1978)) was added and the resulting mixture was stirred at room temperature overnight. The reaction mixture was then diluted with 150 ml ethyl acetate and the resulting mixture was washed with 5--60 ml water and then with 60 ml saturated aqueous sodium chloride solution. The ethyl acetate solution was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The resulting oil was chromatographed on 600 g silica gel, eluting with 7:3 hexane/methylene chloride to yield 9.0 g (81% yield) of the desired product as an oil.

Workup

  1. washthe resulting mixture was washed with 5--60 ml water
  2. dry with materialThe ethyl acetate solution was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resulting oil was chromatographed on 600 g silica gel
  6. washeluting with 7:3 hexane/methylene chloride

Sources & evidence

ORD record
ord-b09bc1dfdba047afa1626cea6d710af3
Source dataset
uspto-grants-1994_11
Patent number
US05362878

Reaction notes

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