Water → 4-(2-hydroxyphenyl)-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile

HRID 892595Notes

Reaction equation

HRID 892595 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:14]2[CH:15]=[C:16]([C:19]#[N:20])[CH:17]=[CH:18][C:13]=2[O:12][C:11]([CH3:22])([CH3:21])[CH:10]=1.C[S-].[Na+].C(OCC)C.O>CN(C)C=O>[OH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:14]2[CH:15]=[C:16]([C:19]#[N:20])[CH:17]=[CH:18][C:13]=2[O:12][C:11]([CH3:22])([CH3:21])[CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 4378561Sodium methanethiolateHCID 19895586HCID 19895586, compound

Product 1

HCID 198956744-(2-hydroxyphenyl)-2,2-dimethyl-2H-1-benzopyran-6-carbonitrileYield 21.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.02 g of 4-(2-methoxyphenyl)-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile and 736 mg of sodium methanethiolate were heated at reflux in 10 ml of dimethylformamide under a nitrogen atmosphere for 1.5 hours and then poured into a mixture of diethyl ether and water. The organic phase was separated, dried over sodium sulphate and evaporated. The residue was chromatographed on silica gel using petroleum ether/ethyl acetate (3:1) for the elution. The resulting solid was recrystallized from diethyl ether/petroleum ether to give 210 mg of 4-(2-hydroxyphenyl)-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile of melting point 139°-140° C.

Workup

  1. customThe organic phase was separated
  2. dry with materialdried over sodium sulphate
  3. customevaporated
  4. customThe residue was chromatographed on silica gel
  5. washfor the elution
  6. customThe resulting solid was recrystallized from diethyl ether/petroleum ether

Sources & evidence

ORD record
ord-6debe740667647a1969cf5aa2e68f6f1
Source dataset
uspto-grants-1992_06
Patent number
US05118694

Reaction notes

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