Lithium borohydride → HCID 59395049, compound

HRID 383419Notes

Reaction equation

HRID 383419 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-3572d5ce6e894416a8b8f8a882018701
Source dataset
uspto-grants-2013_02
Patent number
US08367660B2

Reaction notes

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