Dimethylformamide → 2-Ethylhexyl 3-{[5-(benzyloxy)-2-nitrophenyl]sulfanyl}propanoate

HRID 1026268Notes

Reaction equation

HRID 1026268 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[C:11](F)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C.[SH:30][CH2:31][CH2:32][C:33]([O:35][CH2:36][CH:37]([CH2:42][CH3:43])[CH2:38][CH2:39][CH2:40][CH3:41])=[O:34]>C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[C:11]([S:30][CH2:31][CH2:32][C:33]([O:35][CH2:36][CH:37]([CH2:42][CH3:43])[CH2:38][CH2:39][CH2:40][CH3:41])=[O:34])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 926402-Ethylhexyl 3-mercaptopropionateHCID 221807044-Benzyloxy-2-fluoro-1-nitrobenzene

Product 1

HCID 580473802-Ethylhexyl 3-{[5-(benzyloxy)-2-nitrophenyl]sulfanyl}propanoate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 4-(benzyloxy)-2-fluoro-1-nitrobenzene (2.00 g), potassium carbonate (1.23 g) and DMF (11 mL) was added dropwise 2-ethylhexyl 3-sulfanylpropanoate (2.02 mL), and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate, and washed with saturated brine. The obtained organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound as a yellow liquid (3.60 g).

Workup

  1. washwashed with saturated brine
  2. dry with materialThe obtained organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-6e95f826fae643a49b9b5ca277e8be5a
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

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