Sodium borohydride → HCID 57528604, compound

HRID 500525Notes

Reaction equation

HRID 500525 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:12][N:11]=[C:10]([C:13](=[O:15])[CH3:14])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:12][N:11]=[C:10]([CH:13]([OH:15])[CH3:14])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 467019251-[5-(3-Chlorophenyl)-1,2-oxazol-3-yl]ethan-1-one

Product 1

HCID 57528604HCID 57528604, compoundYield 109.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a screw cap vial equipped with stir bar added the title compound of Example 6.1 (100 mg, 0.45 mmol), sodium borohydride (34 mg, 0.90 mmol) and methanol (3 mL). The resulting mixture was stirred at room temperature for 3 h. The reaction was quenched with water (30 mL) and brine (30 mL), extracted with dichloromethane (3 times 30 mL). The combined organic phase was dried (sodium sulfate), filtered and concentrated, in vacuo to isolate the title compound as a white solid (110 mg).

Workup

  1. customIn a screw cap vial
  2. customequipped
  3. stirringThe resulting mixture was stirred at room temperature for 3 h
  4. customThe reaction was quenched with water (30 mL) and brine (30 mL)
  5. extractionextracted with dichloromethane (3 times 30 mL)
  6. dry with materialThe combined organic phase was dried (sodium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated, in vacuo

Sources & evidence

ORD record
ord-38058b5b35264816b507ccc78975b40c
Source dataset
uspto-grants-2010_08
Patent number
US07772235B2

Reaction notes

Loading…