Sodium borohydride → HCID 63758128, compound

HRID 1476674Notes

Reaction equation

HRID 1476674 reaction equation
[CH2:1]([O:4][CH2:5][C:6]1[N:10]=[C:9]([C:11](OC)=[O:12])[O:8][N:7]=1)[CH2:2][CH3:3].[BH4-].[Na+]>CO>[CH2:1]([O:4][CH2:5][C:6]1[N:10]=[C:9]([CH2:11][OH:12])[O:8][N:7]=1)[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 67258288HCID 67258288, compound

Product 1

HCID 63758128HCID 63758128, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 3-(propoxymethyl)-1,2,4-oxadiazole-5-carboxylate (2.05 g) in MeOH is added sodium borohydride (386 mg) at −10° C. and the mixture is stirred for 15 min at this temperature. The reaction mixture is quenched with ice, stirred for 20 min and extracted with EtOAc three times. The combined organic phases are dried over sodium sulfate and concentrated under reduced pressure. The resulting residue is purified by flash column chromatography (silica gel) to give the title compound as a solid.

Workup

  1. customThe reaction mixture is quenched with ice
  2. stirringstirred for 20 min
  3. extractionextracted with EtOAc three times
  4. dry with materialThe combined organic phases are dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue is purified by flash column chromatography (silica gel)

Sources & evidence

ORD record
ord-fcdd68b9947744f29fd6465240dbb57a
Source dataset
uspto-grants-2015_04
Patent number
US09018175B2

Reaction notes

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