HCID 20093009, compound → HCID 20093029, compound

HRID 248403Notes

Reaction equation

HRID 248403 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-4f436a41f1214775bf1965b304fec85f
Source dataset
uspto-grants-1993_05
Patent number
US05210092

Reaction notes

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