Phosphorus oxychloride → 1-(5-Methoxy-1-methyl-1H-indol-3-yl)ethan-1-one

HRID 1194348

Reaction equation

HRID 1194348 reaction equation
P(Cl)(Cl)(Cl)=O.[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([CH3:17])[CH:12]=[CH:11]2.[CH3:18][C:19](N(C)C)=[O:20]>>[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([CH3:17])[CH:12]=[C:11]2[C:19](=[O:20])[CH3:18]

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 31374Dimethylacetamide2×HCID 8198645-methoxy-1-methyl-1H-indole

Product 1

HCID 212700281-(5-Methoxy-1-methyl-1H-indol-3-yl)ethan-1-one

Procedure

Phosphoryl chloride (1.05 ml) was added dropwise to ice-cooled dimethylacetamide (10 ml) and the solution was stirred, in ice, for 5 min. A solution of 5-methoxy-1-methyl-1H-indole (1.4 g) in dimethylacetamide (5 ml) was added dropwise, and the resulting solution was stirred at 85° for 2 h, then cooled, and partitioned between sodium carbonate (2N; 100 ml) and ethyl acetate (2×100 ml). The combined organic extracts were washed with water (2×100 ml), dried and evaporated in vacuo. The residue was purified by FCC eluting with ethyl acetate to give a solid which was crystallised from a mixture of ethyl acetate and hexane to give the title compound (0.6 g), m.p. 167°-168°.

Workup

  1. stirringthe resulting solution was stirred at 85° for 2 h
  2. temperaturecooled
  3. custompartitioned between sodium carbonate (2N; 100 ml) and ethyl acetate (2×100 ml)
  4. washThe combined organic extracts were washed with water (2×100 ml)
  5. customdried
  6. customevaporated in vacuo
  7. customThe residue was purified by FCC
  8. washeluting with ethyl acetate
  9. customto give a solid which
  10. customwas crystallised from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-d2e74f65075e4eac9baefee2ba2a5c3d
Source dataset
uspto-grants-1989_03
Patent number
US04814344

Linked notes

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