Acetic Anhydride → HCID 20144477, compound

HRID 649010Notes

Reaction equation

HRID 649010 reaction equation
B(F)(F)F.[CH3:5][CH2:6][O:7]CC.[CH3:10][C:11]1[C:16]2[S:17][CH:18]=[CH:19][C:15]=2[CH:14]=[CH:13][CH:12]=1.CC(OC(C)=O)=O>>[C:6]([C:19]1[C:15]2[CH:14]=[CH:13][CH:12]=[C:11]([CH3:10])[C:16]=2[S:17][CH:18]=1)(=[O:7])[CH3:5]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 8000Boron trifluoride etherateHCID 64285417-Methyl-1-benzothiophene

Product 1

HCID 20144477HCID 20144477, compound

Procedure

420 mg of borontrifluoride-etherate are added to a mixture of 2 g of 7-methylbenzo[b]thiophene and 1.4 ml acetanhydride at 50° and the mixture warmed to 60° for 80 minutes. The resulting mixture is poured onto ice, extracted with ether and the organic phase washed, dried and concentrated on a rotary evaporator. The residue is chromatographed on silica gel (eluant: n-hexane) to obtain the title compound, contaminated with the 2-acetylisomer, as an oil for direct further reaction.

Workup

  1. temperaturethe mixture warmed to 60° for 80 minutes
  2. additionThe resulting mixture is poured onto ice
  3. extractionextracted with ether
  4. washthe organic phase washed
  5. customdried
  6. concentrationconcentrated on a rotary evaporator
  7. customThe residue is chromatographed on silica gel (eluant: n-hexane)

Sources & evidence

ORD record
ord-5b9bf88380354f209f686f0ea2ed7211
Source dataset
uspto-grants-1988_04
Patent number
US04737516

Reaction notes

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