Potassium Carbonate → 2-Ethylhexyl 3-{[4-(benzyloxy)-2-nitrophenyl]sulfanyl}propanoate

HRID 1888721Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](Cl)=[C:11]([N+:16]([O-:18])=[O:17])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[SH:19][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH:26]([CH2:31][CH3:32])[CH2:27][CH2:28][CH2:29][CH3:30])=[O:23].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([S:19][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH:26]([CH2:31][CH3:32])[CH2:27][CH2:28][CH2:29][CH3:30])=[O:23])=[C:11]([N+:16]([O-:18])=[O:17])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A suspension of 4-(benzyloxy)-1-chloro-2-nitrobenzene (5.00 g, 19.0 mmol), 2-ethylhexyl 3-sulfanylpropanoate (4.55 g, 20.9 mmol) and potassium carbonate (3.93 g, 28.4 mmol) in DMF (20 mL) was stirred under heating at 60° C. for 16 hr. The reaction mixture was diluted with ethyl acetate, and the mixture was washed with water, 10% aqueous potassium carbonate solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by 15 silica gel column chromatography (hexane:ethyl acetate=19:1 to 3:1) to give the title compound (5.67 g, yield 67%) as an oil.

Workup

washthe mixture was washed with water, 10% aqueous potassium carbonate solution and saturated brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated under reduced pressure
customthe obtained residue was purified by 15 silica gel column chromatography (hexane:ethyl acetate=19:1 to 3:1)

Sources & evidence

ORD record: ord-2708bf852bb34a40bfff00542103b30c
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501804B2

Reaction notes

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