Sodium borohydride → [5-(3-Chlorophenyl)isoxazol-3-yl]methanol

HRID 1453798Notes

Reaction equation

HRID 1453798 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([C:10]2[O:14][N:13]=[C:12]([C:15](OCC)=[O:16])[CH:11]=2)[CH:7]=[CH:8][CH:9]=1>CO>[Cl:3][C:4]1[CH:5]=[C:6]([C:10]2[O:14][N:13]=[C:12]([CH2:15][OH:16])[CH:11]=2)[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 46929188Ethyl 5-(3-chlorophenyl)isoxazole-3-carboxylate

Product 1

HCID 57528605[5-(3-Chlorophenyl)isoxazol-3-yl]methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Sodium borohydride (96.7 g, 2.6 mol) was slowly added to a solution of ethyl 5-(3-chlorophenyl)isoxazole-3-carboxylate (214.5 g, 0.85 mol) in methanol (2.5 L) at 0° C. The reaction mixture was heated at 50° C. for 2 h and was quenched with EtOAc at r.t. Most of the solvent was distilled off and to the remaining crude was added EtOAc. The organic layer was washed with water, saturated brine and concentrated to give the title compound, which was used directly in the next step. MS (M++1)=210.

Workup

  1. customwas quenched with EtOAc at r.t
  2. distillationMost of the solvent was distilled off and to the remaining crude
  3. additionwas added EtOAc
  4. washThe organic layer was washed with water, saturated brine
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-12c5278033dc4b20816c3773871ca6c2
Source dataset
uspto-grants-2009_01
Patent number
US07476684B2

Reaction notes

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