Sodium borohydride → [3-(4-Benzyloxyphenyl)-[1,2,4]thiadiazol-5-yl]-methanol

HRID 453106

Reaction equation

HRID 453106 reaction equation
C([O:3][C:4]([C:6]1[S:10][N:9]=[C:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:13][CH:12]=2)[N:7]=1)=O)C.[BH4-].[Na+]>CCO>[CH2:18]([O:17][C:14]1[CH:15]=[CH:16][C:11]([C:8]2[N:7]=[C:6]([CH2:4][OH:3])[S:10][N:9]=2)=[CH:12][CH:13]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 595495323-(4-Benzyloxyphenyl)-[1,2,4]thiadiazole-5-carboxylic acid ethyl ester

Product 1

HCID 59549522[3-(4-Benzyloxyphenyl)-[1,2,4]thiadiazol-5-yl]-methanolYield 30%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-(4-benzyloxyphenyl)-[1,2,4]thiadiazole-5-carboxylic acid ethyl ester (0.20 g, 0.59 mmol) in EtOH (20 ml) was added sodium borohydride (0.44 g, 1.17 mmol) portion wise and the resulting reaction mixture was stirred at room temperature for 2 h. After the completion of the reaction (TLC monitoring), the reaction mass was cooled to 0° C., quenched it with 5 ml of water and concentrated under vacuum. Added 75 ml water and extracted with ethyl acetate (3×30 ml). The combined organic layer was dried over Na2SO4, filtered and concentrated under vacuum. The crude residue was purified over silica gel (100-200 M, 30% EtOAc-Hexane) to get the desired product (0.052 g, 30%).

Workup

  1. customthe resulting reaction mixture
  2. customAfter the completion of the reaction (TLC monitoring)
  3. temperaturethe reaction mass was cooled to 0° C.
  4. customquenched it with 5 ml of water
  5. concentrationconcentrated under vacuum
  6. additionAdded 75 ml water
  7. extractionextracted with ethyl acetate (3×30 ml)
  8. dry with materialThe combined organic layer was dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated under vacuum
  11. customThe crude residue was purified over silica gel (100-200 M, 30% EtOAc-Hexane)

Sources & evidence

ORD record
ord-903234933b774e1e8e71b928d59b05de
Source dataset
uspto-grants-2013_07
Patent number
US08492414B2

Linked notes

Loading…