Dimethyl Sulfoxide → HCID 54074783, compound

HRID 267832Notes

Reaction equation

HRID 267832 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 is 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 is added 270 mg. (1.65 mm) of 5-fluoro-2-methyl-1-indanone in 2 ml. of DMSO. The solution is heated at 75°C for 15.5 hours. Benzene and water are added and the benzene layer is washed five times with water. The benzene layer is dried over Na2SO4 and evaporated to dryness under vacuum. The weight is 915.6 mg. This material is eluted through 8 g. of silica gel with benzene to remove triphenylphosphine oxide. The eluate weights 372 mg. after removal of solvent. This is rechromatographed through 15 g. of silica gel using hexane and 95.9 mg. of 5-fluoro-2-methyl-1-(p-methylthiobenzylidene)-indane is isolated, melting point 67°-70°C.

Workup

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

Sources & evidence

ORD record
ord-2109a51794c743e4be107d5475ee5a84
Source dataset
uspto-grants-1976_03
Patent number
US03944600

Reaction notes

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