Sodium borohydride → HCID 63758128, compound
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
Product 1
Reagents, catalysts & solvents 1
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
- customThe reaction mixture is quenched with ice
- stirringstirred for 20 min
- extractionextracted with EtOAc three times
- dry with materialThe combined organic phases are dried over sodium sulfate
- concentrationconcentrated under reduced pressure
- 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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