Potassium Carbonate → HCID 57859812, compound

HRID 68228Notes

Reaction equation

HRID 68228 reaction equation
[CH3:1][S:2][C:3]1[CH:4]=[C:5]([SH:9])[CH:6]=[CH:7][CH:8]=1.F[C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O>[CH3:1][S:2][C:3]1[CH:4]=[C:5]([S:9][C:11]2[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][CH:12]=2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 680234-FluorobenzaldehydeHCID 12763272HCID 12763272, compound

Product 1

HCID 57859812HCID 57859812, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 3-(methylthio)benzenethiol (19.9 g, 127.3 mmol), prepared as indicated in Rumpf, P., Bull. soc. chim. (1940), 7, pp. 632-4, in acetonitrile (60 mL) was treated with 4-fluorobenzaldehyde (13.4 mL, 127 mmol) followed by potassium carbonate (19.4 g, 140 mmol). After stirring at ambient temperature for 18 hours the suspension was diluted with water (200 mL) and extracted with ethyl acetate (3-fold 300 mL). The combined organic extracts were washed with brine (2-fold 100 mL) and dried (magnesium sulphate) and the solvent removed in vacuo to give a colourless oil. The crude oil was purified by flash column chromatography on silica gel eluting with heptane:ethyl acetate (1:0 changing to 9:1, by volume) to give the title compound as a colourless oil, 33% yield, 10.8 g.

Workup

  1. extractionextracted with ethyl acetate (3-fold 300 mL)
  2. washThe combined organic extracts were washed with brine (2-fold 100 mL)
  3. dry with materialdried (magnesium sulphate)
  4. customthe solvent removed in vacuo
  5. customto give a colourless oil
  6. customThe crude oil was purified by flash column chromatography on silica gel eluting with heptane:ethyl acetate (1:0 changing to 9:1, by volume)

Sources & evidence

ORD record
ord-40be5f2965454529abf9aee0df6694af
Source dataset
uspto-grants-2014_09
Patent number
US08822439B2

Reaction notes

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