HCID 20093009, compound → HCID 20093029, compound

HRID 1586826Notes

Reaction equation

HRID 1586826 reaction equation
[C:1]([CH2:3][O:4][C:5]1[CH:19]=[CH:18][CH:17]=[CH:16][C:6]=1[C:7]([C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)=O)#[N:2].CC(C)([O-])C.[K+]>C1C=CC=CC=1>[CH3:15][C:12]1[CH:13]=[CH:14][C:9]([C:7]2[C:6]3[CH:16]=[CH:17][CH:18]=[CH:19][C:5]=3[O:4][C:3]=2[C:1]#[N:2])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 20093009HCID 20093009, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 20093029HCID 20093029, compoundYield 10.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a mixture of 2-cyanomethoxy-4'-methylbenzophenone (18.6 g) and molecular sieves (18 g) in benzene (270 ml) was added potassium tert-butoxide (8.31 g) in one portion at ambient temperature. After stirring at the same temperature for one hour, the mixture was filtered off. The filtrate was washed with diluted hydrochloric acid, dried, and concentrated in vacuo. The residue was purified by flash column chromatography to yield 3-(4-methylphenyl)benzo[b]furan-2-carbonitrile (1.82 g) as white crystals.

Workup

  1. filtrationthe mixture was filtered off
  2. washThe filtrate was washed with diluted hydrochloric acid
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-54c5e620e4674117ad4d0b7423b1fb69
Source dataset
uspto-grants-1993_06
Patent number
US05215994

Reaction notes

Loading…