Water → HCID 14407228, compound

HRID 1389180Notes

Reaction equation

HRID 1389180 reaction equation
Br[CH2:2][C:3](=[O:24])[CH:4]=[P:5]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:25]1([SH:31])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[Na].O>C(O)C>[O:24]=[C:3]([CH2:2][S:31][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH:4]=[P:5]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7969ThiophenolHCID 5360545SodiumHCID 12546501HCID 12546501, compound

Product 1

HCID 14407228HCID 14407228, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Bromo-2-oxopropylidenetriphenylphosphorane (17.85 g) was added to a solution of thiophenol (5.22 g; 4.86 ml) in anhydrous ethanol (70 ml) containing sodium (1.09 g). The mixture was heated at reflux for 150 minutes and was then poured into a mixture of ice and water (250 ml). The mixture was then extracted with dichloromethane and the extract was washed with dilute aqueous sodium hydroxide solution (2 N) and then with water, and was dried over magnesium sulphate. Evaporation of the solvent gave a residual oil which was triturated with petroleum ether (b.p. 40°-60° C.), and the resulting crude solid was recrystallised from a mixture of toluene and petroleum ether (b.p. 60°-80° C.) to give 2-oxo-3-phenylthiopropylidenetriphenylphosphorane (14.2 g) in the form of cream prisms, m.p. 132°-134° C. [elemental analysis: C, 76.4; H, 5.3; P, 7.3; S, 7.7%. C27H23OPS requires C, 76.0; H, 5.4; P, 7.3; S, 7.5%. νmax 715, 740, 750, 1110, 1385, 1440, 1485 and 1550 cm-1 ].

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 150 minutes
  3. extractionThe mixture was then extracted with dichloromethane
  4. washthe extract was washed with dilute aqueous sodium hydroxide solution (2 N)
  5. dry with materialwith water, and was dried over magnesium sulphate
  6. customEvaporation of the solvent
  7. customgave a residual oil which
  8. customwas triturated with petroleum ether (b.p. 40°-60° C.)
  9. customthe resulting crude solid was recrystallised from a mixture of toluene and petroleum ether (b.p. 60°-80° C.)

Sources & evidence

ORD record
ord-81e28869151c4f9c97862ad5fd71698a
Source dataset
uspto-grants-1981_01
Patent number
US04243683

Reaction notes

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