Sodium borohydride → 3-[5-(Phenylmethyl)-1,2,4-oxadiazol-3-yl]-1-propanol

HRID 1097678Notes

Reaction equation

HRID 1097678 reaction equation
[C:1]1([CH2:7][C:8]2[O:12][N:11]=[C:10]([CH2:13][CH2:14][CH:15]=[O:16])[N:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>CO>[C:1]1([CH2:7][C:8]2[O:12][N:11]=[C:10]([CH2:13][CH2:14][CH2:15][OH:16])[N:9]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 866431133-[5-(Phenylmethyl)-1,2,4-oxadiazol-3-yl]propanal

Product 1

HCID 593958023-[5-(Phenylmethyl)-1,2,4-oxadiazol-3-yl]-1-propanolYield 59%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of crude 3-[5-(phenylmethyl)-1,2,4-oxadiazol-3-yl]propanal (3.76 g, 17.4 mmol) in MeOH (60 ml) was cooled to 0° C. and sodium borohydride (0.724 g, 19.1 mmol) added portionwise over 30 min. The cooling bath was removed and the solution stirred for a further 1 h then partitioned between 1M HCl and EtOAc. The organic layer was separated and the aqueous extracted with EtOAc. The combined extracts were washed with brine, dried and concentrated to an orange liquid. This was purified on a 50 g silica SPE eluting with cyclohexane/EtOAc (20% to 80% gradient elution) to provide the title compound as a yellow oil (2.24 g).

Workup

  1. customThe cooling bath was removed
  2. customthen partitioned between 1M HCl and EtOAc
  3. customThe organic layer was separated
  4. extractionthe aqueous extracted with EtOAc
  5. washThe combined extracts were washed with brine
  6. customdried
  7. concentrationconcentrated to an orange liquid
  8. customThis was purified on a 50 g silica SPE
  9. washeluting with cyclohexane/EtOAc (20% to 80% gradient elution)

Sources & evidence

ORD record
ord-1849eeb0e6884b41835449b03b4ddc8b
Source dataset
uspto-grants-2012_03
Patent number
US08143264B2

Reaction notes

Loading…