Sodium borohydride → HCID 21907364, compound

HRID 491747Notes

Reaction equation

HRID 491747 reaction equation
[BH4-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:22]=[O:23])[C:8]2[O:12][C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)=[N:10][C:9]=2[CH:21]=1>CO>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH2:22][OH:23])[C:8]2[O:12][C:11]([C:13]3[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=3)=[N:10][C:9]=2[CH:21]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 85839547HCID 85839547, compound

Product 1

HCID 21907364HCID 21907364, compoundYield 83.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (66.8 mg, 1.76 mmol) was added into a solution of 5-methoxy-2-(4-methoxyphenyl)-1,3-benzoxazole-7-carbaldehyde (250 mg, 0.88 mmol) in anhydrous MeOH (8 mL) at 0° C. The reaction mixture was stirred for 30 min and then evaporated in vacuum. The residue was dissolved in diethyl ether and washed with water and brine, dried over MgSO4 and filtered. Evaporation and flash chromatography (50% EtOAc/petroleum ether) gave (210 mg, 83%) of the product, which was used directly in the next reaction.

Workup

  1. customevaporated in vacuum
  2. dissolutionThe residue was dissolved in diethyl ether
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customEvaporation and flash chromatography (50% EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-20b48f54dae4459e8957036dcfcb2072
Source dataset
uspto-grants-2009_05
Patent number
US07531564B2

Reaction notes

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