Thiophenol → 6-Phenylsulfanyl-hexa-2,4-dienoic acid methyl ester

HRID 2245758Notes

Reaction equation

HRID 2245758 reaction equation
[CH3:1][O:2][C:3](=[O:10])[CH:4]=[CH:5][CH:6]=[CH:7][CH2:8]Br.[C:11]1([SH:17])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C>>[CH3:1][O:2][C:3](=[O:10])[CH:4]=[CH:5][CH:6]=[CH:7][CH2:8][S:17][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 3

HCID 7969ThiophenolHCID 8471TriethylamineHCID 54529347Methyl 6-bromohexa-2,4-dienoate

Product 1

HCID 730968226-Phenylsulfanyl-hexa-2,4-dienoic acid methyl esterYield 141.8%

Conditions

Temperature
20 °C

Procedure

To a solution of 6-bromohexa-2,4-dienoic acid methyl ester (0.57 g, 2.8 mmol) and thiophenol (0.28 mL, 2.8 mmol) was added triethylamine (0.43 mL, 3.1 mmol), dropwise, under an atmosphere of nitrogen. The mixture was stirred at 20° C. for one hour. The slurry was then filtered and the filtrate was washed with aqueous sodium hydroxide (1 M) then with brine. The organic layer was dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The residue was subjected to column chromatography (9:1 60-80° C. petroleum ether:diethyl ether) to give the title compound (0.93 g, 88%) as a clear oil.

Workup

  1. filtrationThe slurry was then filtered
  2. washthe filtrate was washed with aqueous sodium hydroxide (1 M)
  3. dry with materialThe organic layer was dried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customwas subjected to column chromatography (9:1 60-80° C. petroleum ether:diethyl ether)

Sources & evidence

ORD record
ord-8366e3b4eaba4a4599af20067df0ef33
Source dataset
uspto-grants-2010_03
Patent number
US07683185B2

Reaction notes

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