Water → 5-(4-Cyanophenyl)-3-hydroxymethyl-1,2,4-oxadiazole

HRID 54540Notes

Reaction equation

HRID 54540 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][N:12]=[C:11]([C:14](OCC)=[O:15])[N:10]=2)=[CH:5][CH:4]=1)#[N:2].O1CCCC1.[BH4-].[Na+].O>CO>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[O:13][N:12]=[C:11]([CH2:14][OH:15])[N:10]=2)=[CH:7][CH:8]=1)#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 199591483-Ethoxycarbonyl-5-(4-cyanophenyl)-1,2,4-oxadiazole

Product 1

HCID 199591695-(4-Cyanophenyl)-3-hydroxymethyl-1,2,4-oxadiazoleYield 96.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-(4-cyanophenyl)-3-ethoxycarbonyl-1,2,4-oxadiazole (5.0 g) in methanol (50 ml)--tetrahydrofuran (50 ml) was added sodium borohydride (0.93 g) at 0° C. After stirring at 5°-10° C. for 1 hour, the mixture was poured into water and extracted with ethyl acetate. The extract was washed with water and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was recrystallized from diethyl ether to give 5-(4-cyanophenyl)-3-hydroxymethyl-1,2,4-oxadiazole (4.0 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-008dbd1864a042c18c6448049da19547
Source dataset
uspto-grants-1997_04
Patent number
US05622976

Reaction notes

Loading…