Methanol → HCID 20068977, compound

HRID 982013Notes

Reaction equation

HRID 982013 reaction equation
[CH3:1][S:2][C:3]1[S:4][C:5]([C:10]#N)=[CH:6][C:7]=1C#N.[H-].C([Al+]CC(C)C)C(C)C.[CH3:22][OH:23].S(=O)(=O)(O)[OH:25]>C1(C)C=CC=CC=1>[CH3:1][S:2][C:3]1[S:4][C:5]([CH:10]=[O:25])=[CH:6][C:7]=1[CH:22]=[O:23]

Participants

6

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 20068973HCID 20068973, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 20068977HCID 20068977, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a suspension of 7.20 g of 2-methylthio-3,5-dicyanothiophene, obtained according to Example IV (a), in 120 ml of dry toluene is added, while stirring and under a nitrogen blanket, 75 ml of a 20% solution of diisobutyl aluminumhydride in toluene. The reaction mixture is stirred for two hours, after which 12 ml of methanol is added under cooling in ice. The reaction mixture is stirred in ice plus conc. sulphuric acid till a clear solution. The toluene phase is separated and the water phase washed twice with toluene. The combined organic phase is washed with water, dried, filtered and evaporated. The residue is recrystallized from ethanol yielding 2-methylthio-3,5-diformylthiophene in a quantity of 3.0 g; melting point 135°-137° C.

Workup

  1. customobtained
  2. additionis added
  3. temperatureunder cooling in ice
  4. stirringThe reaction mixture is stirred in ice
  5. customThe toluene phase is separated
  6. washthe water phase washed twice with toluene
  7. washThe combined organic phase is washed with water
  8. customdried
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-1fc6731e84d24f82bf961995d9787411
Source dataset
uspto-grants-1991_02
Patent number
US04994485

Reaction notes

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