Potassium Carbonate → [4-nitro-3-[[(tetrahydro-2H-pyran-2-yl)oxy]methyl]phenyl] phenylmethanone

HRID 2247902Notes

Reaction equation

HRID 2247902 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)C#N)=[CH:6][C:5]=1[CH2:19][O:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][O:22]1)([O-:3])=[O:2].C(=O)([O-])[O-:28].[K+].[K+]>CN(C)C(=O)C>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:28])=[CH:6][C:5]=1[CH2:19][O:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][O:22]1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 151770844-nitro-alpha-phenyl-3-[[(tetrahydro-2H-pyran-2-yl)oxy]methyl]benzeneacetonitrile

Product 1

HCID 15177085[4-nitro-3-[[(tetrahydro-2H-pyran-2-yl)oxy]methyl]phenyl] phenylmethanoneYield 98.6%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A mixture of 26.2 parts of intermediate 55, namely 4-nitro-α-phenyl-3-[[(tetrahydro-2H-pyran-2-yl)oxy]methyl]benzeneacetonitrile, 10.2 parts of potassium carbonate and 376 parts of N,N-dimethylacetamide was stirred at room temperature while air was bubbled through. The reaction mixture was poured into water and the product was extracted with 2,2'-oxybispropane. The extract was dried, filtered and evaporated, yielding 25 parts (98.6%) of [4-nitro-3-[[(tetrahydro-2H-pyran-2-yl)oxy]methyl]phenyl] phenylmethanone (interm. 56).

Workup

  1. customwas bubbled through
  2. additionThe reaction mixture was poured into water
  3. extractionthe product was extracted with 2,2'-oxybispropane
  4. customThe extract was dried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-6532b02834f142438ec89d9880ba7ea4
Source dataset
uspto-grants-1991_08
Patent number
US05037829

Reaction notes

Loading…