HCID 23333840, compound → HCID 23333827, compound

HRID 904226Notes

Reaction equation

HRID 904226 reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]1[CH:12]=[CH:11][C:10]([C:13]2([CH3:16])[CH2:15][O:14]2)=[CH:9][CH:8]=1>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]1[CH:12]=[CH:11][C:10]([CH:13]([CH3:16])[CH:15]=[O:14])=[CH:9][CH:8]=1

Participants

3

Reactant 1

HCID 23333840HCID 23333840, compound

Product 1

HCID 23333827HCID 23333827, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In 25 ml of acetonitrile was dissolved 5.0 g (0.0232 mole) of 4-(3-methyl-2-thienyl)acetophenone, followed by the addition of 8.7 g (0.046 mole) of trimethylsulfonium methyl sulfate. To the mixture was added with stirring at room temperature 2.5 g (0.0464 mole) of sodium methylate. After having been stirred for one hour, the mixture was freed from the solvent by distillation under reduced pressure. To the residue was added 20 ml of toluene, and the solution was washed several times with water, dried over anhydrous magnesium sulfate, and freed from the solvent by distillation under reduced pressure to obtain 5.2 g (97.4% yield) of almost pure oily 2-[4-(3-methyl-2-thienyl)phenyl]-2-methyloxirane. This oxirane compound was dissolved in 25 ml of toluene, admixed with 0.5 g of powdered Molecular Sieves 4A, and refluxed for one hour. The Molecular Sieves was removed by filtration and the filtrate was freed from the solvent by distillation under reduced pressure to obtain 5.1 g (98% yield) of oily 2-[4-(3-methyl-2-thienyl)phenyl]propionaldehyde.

Workup

  1. temperaturerefluxed for one hour
  2. customThe Molecular Sieves was removed by filtration
  3. distillationthe filtrate was freed from the solvent by distillation under reduced pressure

Sources & evidence

ORD record
ord-7cb7ce26c4c84c98925b6b39f976ebcf
Source dataset
uspto-grants-1980_10
Patent number
US04230719

Reaction notes

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