Lithium borohydride → HCID 59395049, compound

HRID 471989Notes

Reaction equation

HRID 471989 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:18]([O-:20])=[O:19])=[C:6]([C:8]2[O:12][N:11]=[C:10]([C:13](OCC)=[O:14])[N:9]=2)[CH:7]=1.[BH4-].[Li+]>C(O)C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:18]([O-:20])=[O:19])=[C:6]([C:8]2[O:12][N:11]=[C:10]([CH2:13][OH:14])[N:9]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 59394968HCID 59394968, compound

Product 1

HCID 59395049HCID 59395049, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 5-(5-methyl-2-nitro-phenyl)-1,2,4-oxadiazole-3-carboxylate (60 mg, 0.22 mmol) was dissolved in ethanol (3 mL) and treated with lithium borohydride (9 mg, 0.4 mmol) at room temperature. The mixture was stirred for 1 h then quenched with saturated ammonium chloride and extracted into dichloromethane. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to provide (5-(5-methyl-2-nitrophenyl)-1,2,4-oxadiazol-3-yl)methanol (35 mg, 69% yield). LC/MS m/z 236.0 [M+H]+.

Workup

  1. customthen quenched with saturated ammonium chloride
  2. extractionextracted into dichloromethane
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0ddf72abed244d03b79a3b9d8bdc3540
Source dataset
uspto-grants-2014_01
Patent number
US08633189B2

Reaction notes

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