Sodium borohydride → HCID 14990561, compound

HRID 2248311Notes

Reaction equation

HRID 2248311 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:21]=[CH:20][C:13]3[N:14]([CH:17]([CH3:19])[CH3:18])[N:15]=[N:16][C:12]=3[CH:11]=2)=[O:9])=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:10]2[CH:21]=[CH:20][C:13]3[N:14]([CH:17]([CH3:18])[CH3:19])[N:15]=[N:16][C:12]=3[CH:11]=2)[OH:9])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 14990560HCID 14990560, compound

Product 1

HCID 14990561HCID 14990561, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 17 parts of (4fluorophenyl) [1-(1-methylethyl)-1H-benzotriazol-5-yl]methanone in 80 parts of ethanol were added 3.4 parts of sodium tetrahydroborate. After stirring for 1 hour at room temperature, the reaction mixture was neutralized to pH 7. The reaction mixture was concentrated and the product was extracted with ethyl acetate. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of dichloromethane and methanol (98:2 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 10.7 parts (62.5%) of α-(4-fluorophenyl)-1-(1-methylethyl)-1H-benzotriazole-5-methanol as a residue (int. 4).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionthe product was extracted with ethyl acetate
  3. customThe extract was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography over silica gel using
  7. additiona mixture of dichloromethane and methanol (98:2 by volume) as eluent
  8. customThe pure fractions were collected
  9. customthe eluent was evaporated

Sources & evidence

ORD record
ord-96d275676a2446b0a13a9a80dc7a4783
Source dataset
uspto-grants-1991_08
Patent number
US05039677

Reaction notes

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