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

HRID 453095Notes

Reaction equation

HRID 453095 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][CH3:18])=[CH:13][CH:12]=2)[N:7]=1)=O)C.[BH4-].[Na+]>CO>[CH3:18][O:17][C:14]1[CH:13]=[CH:12][C:11]([C:8]2[N:7]=[C:6]([CH2:4][OH:3])[S:10][N:9]=2)=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 12601460Ethyl 3-(4-methoxyphenyl)-[1,2,4]thiadiazole-5-carboxylate

Product 1

HCID 25132885[3-(4-Methoxyphenyl)-[1,2,4]thiadiazol-5-yl]-methanolYield 43%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-(4-methoxyphenyl)-[1,2,4]thiadiazole-5-carboxylic acid ethyl ester (0.24 g, 0.90 mmol) in MeOH (10 ml) was added sodium borohydride (0.058 g, 1.54 mmol) portion wise. 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 2 ml of water and concentrated under vacuum. Added water (50 ml) and extracted with ethyl acetate (3×50 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, 20% EtOAc-Hexane) to get the product (0.072 g, 43%) that was carried forward to the next step without further purification.

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 2 ml of water
  5. concentrationconcentrated under vacuum
  6. extractionAdded water (50 ml) and extracted with ethyl acetate (3×50 ml)
  7. dry with materialThe combined organic layer was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum
  10. customThe crude residue was purified over silica gel (100-200 M, 20% EtOAc-Hexane)

Sources & evidence

ORD record
ord-e2b1241a7bfc40cd8521af8989048b08
Source dataset
uspto-grants-2013_07
Patent number
US08492414B2

Reaction notes

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