Lithium borohydride → HCID 59395049, compound

HRID 1465139Notes

Reaction equation

HRID 1465139 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, 0.43 mmol) at room temperature. The mixture was stirred for 1 h, then quenched with saturated NH4Cl 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. customquenched with saturated NH4Cl
  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-5815d010a0054bf099d6cfd2fda33187
Source dataset
uspto-grants-2015_04
Patent number
US08999976B2

Reaction notes

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