Water → HCID 18985954, compound

HRID 1608758Notes

Reaction equation

HRID 1608758 reaction equation
C1(C)C=CC(S(O[CH2:11][C@H:12]([C:14]2([OH:19])[CH2:18][CH2:17][CH2:16][CH2:15]2)[CH3:13])(=O)=O)=CC=1.C(N(CC)CC)C.[C:28]1([SH:34])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.O>CN(C)C=O>[C:28]1([S:34][CH2:11][CH:12]([C:14]2([OH:19])[CH2:15][CH2:16][CH2:17][CH2:18]2)[CH3:13])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 4

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

Product 1

HCID 18985954HCID 18985954, compound

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-e9d54a57c2a04e15aa2fb6cee24d39ef
Source dataset
uspto-grants-1995_03
Patent number
US05397775

Reaction notes

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