Dimethyl Sulfoxide → HCID 54074783, compound

HRID 918295Notes

Reaction equation

HRID 918295 reaction equation
CC(C)([O-])C.[K+].CS(C)=O.[Cl-].[CH3:12][S:13][C:14]1[CH:39]=[CH:38][C:17]([CH2:18][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:16][CH:15]=1.[F:40][C:41]1[CH:42]=[C:43]2[C:47](=[CH:48][CH:49]=1)[C:46](=O)[CH:45]([CH3:51])[CH2:44]2>O.C1C=CC=CC=1>[F:40][C:41]1[CH:42]=[C:43]2[C:47](=[CH:48][CH:49]=1)[C:46](=[CH:18][C:17]1[CH:16]=[CH:15][C:14]([S:13][CH3:12])=[CH:39][CH:38]=1)[CH:45]([CH3:51])[CH2:44]2

Participants

7

Reactant 4

HCID 679Dimethyl Sulfoxide3×HCID 30162575-Fluoro-2-methylindan-1-oneHCID 189697944-Methylthiobenzyltriphenylphosphonium chlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 54074783HCID 54074783, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

169 Mg. (1.5 mm) of potassium t-butoxide was dissolved in 2 ml. of DMSO and treated with 651 mg. (1.5 mm) of p-methylthiobenzyltriphenylphosphonium chloride dissolved in 1 ml. of DMSO. To this solution was added 270 mg. (1.65 mm) of 5-fluoro-2-methyl-1-indanone in 2 ml. of DMSO. The solution was heated at 75°C for 15.5 hours. Benzene and water were added and the benzene layer was washed five times with water. The benzene layer was dried over Na2SO4 and evaporated to dryness under vacuum. The weight was 915.6 mg. This material was eluted through 8 g. of silica gel with benzene to remove triphenylphosphine oxide. The eluate weighed 372 mg. after removal of solvent. This was rechromatographed through 15 g. of silica gel using hexane and 95.9 mg. of 5-fluoro-2-methyl-1-(p-methylthiobenzylidene)-indane was isolated, melting point 67° to 70°C.

Workup

  1. additionTo this solution was added 270 mg
  2. washthe benzene layer was washed five times with water
  3. dry with materialThe benzene layer was dried over Na2SO4
  4. customevaporated to dryness under vacuum
  5. washThis material was eluted through 8 g
  6. customof silica gel with benzene to remove triphenylphosphine oxide
  7. customafter removal of solvent
  8. customThis was rechromatographed through 15 g

Sources & evidence

ORD record
ord-b143047bc3e5493aac9b896e2a326bd0
Source dataset
uspto-grants-1976_07
Patent number
US03970693

Reaction notes

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