Water → 6-Chloro-3-(1H-imidazol-1-yl)-3,4-dihydro-2H-1-benzopyran-4-ol

HRID 745976Notes

Reaction equation

HRID 745976 reaction equation
[BH4-].[Na+].[N:3]1([CH:8]2[C:13](=[O:14])[C:12]3[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:11]=3[O:10][CH2:9]2)[CH:7]=[CH:6][N:5]=[CH:4]1.O>CO>[N:3]1([CH:8]2[CH:13]([OH:14])[C:12]3[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:11]=3[O:10][CH2:9]2)[CH:7]=[CH:6][N:5]=[CH:4]1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 129536396-Chloro-3-(1H-imidazol-1-yl)chroman-4-one

Product 1

HCID 129536486-Chloro-3-(1H-imidazol-1-yl)-3,4-dihydro-2H-1-benzopyran-4-olYield 99.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

NaBH4 (1 g) was added portionwise to a solution of 3-(1-imidazolyl)-2,3-dihydro-6-chloro-4H-1-benzopyran-4-one (2.7 g) in MeOH (70 ml) at 5°-10° C. The mixture, stirred at room temperature for 2 hours, added with water (300 ml), extracted with CHCl3, dried and evaporated to dryness gave (2.7 g) 3-(1-imidazolyl)-2,3-dihydro-6-chloro-4H-1-benzopyran-4-ol.

Workup

  1. extractionextracted with CHCl3
  2. customdried
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-b6e61a1e299e489280d1388b271e0bf8
Source dataset
uspto-grants-1986_07
Patent number
US04602022

Reaction notes

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