Water → HCID 22858126, compound

HRID 2260836Notes

Reaction equation

HRID 2260836 reaction equation
C(N([CH2:6][CH3:7])CC)C.[C:8]1([SH:14])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH2:15]>CN(C)C=O>[C:8]1([S:14][CH2:9][C@H:8]([C:7]2([OH:15])[CH2:6][CH2:12][CH2:11][CH2:10]2)[CH3:13])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7969ThiophenolHCID 8471Triethylamine

Product 1

HCID 22858126HCID 22858126, 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. 1H-NMR δ (CDCl3, 500 MHz); 1.24 (3H, d, J=6.3 Hz), 1.53 (1H, br s), 1.56-2.04 (9H), 2.85 (1H, dd, J=12.9 and 10.2 Hz), 3.44 (1H, dd. J=12.9 and 2.8 Hz), 7.28 (1H, t, J=8.0 Hz), 7.39 (2H, t, J=8.0 Hz), 7.46 (2H, d, J=8.0 Hz)

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-a3455a3ef9a7448dbc9d820ebdbfe954
Source dataset
uspto-grants-1995_12
Patent number
US05478955

Reaction notes

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