Water → HCID 22852129, compound

HRID 2396692Notes

Reaction equation

HRID 2396692 reaction equation
[C:1]1([CH3:20])[CH:6]=[CH:5][C:4]([S:7]([O:10][CH2:11][C@H:12]([C:14]2([OH:19])[CH2:18][CH2:17][CH2:16][CH2:15]2)[CH3:13])(=[O:9])=[O:8])=[CH:3][CH:2]=1.C(N(CC)CC)C.C1(S)C=CC=CC=1.O>CN(C)C=O>[C:1]1([CH3:20])[CH:2]=[CH:3][C:4]([S:7]([O:10][CH2:11][C@@H:12]([C:14]2([OH:19])[CH2:18][CH2:17][CH2:16][CH2:15]2)[CH3:13])(=[O:9])=[O:8])=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7969ThiophenolHCID 8471TriethylamineHCID 22858125HCID 22858125, compound

Product 1

HCID 22852129HCID 22852129, compoundYield 91.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4a (3.65 g, 11.9 mmol) and triethylamine (2.5 mL) in N, N-dimethylformamide (18 mL) was added thiophenol (1.8 mL) in one portion. The mixture was stirred at ambient temperature overnight. The mixture was poured into water, and extracted with diethyl ether. The combined organic layers were washed with sodium bicarbonate solution and brine, and dried over sodium sulfate. Filtration and concentration gave 3.26 g of an oily material, which was purified by column chromatography (silica gel 40 g, ethyl acetate in n-hexane, 2.5-20%) to give 2.06 g (73.3%) of 5a, as a pale yellow oil.

Workup

  1. extractionextracted with diethyl ether
  2. washThe combined organic layers were washed with sodium bicarbonate solution and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-83d2d9d7e2d0413c89f1829afac9bbfe
Source dataset
uspto-grants-1996_02
Patent number
US05494906

Reaction notes

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