Sodium borohydride → (3-(2-(Benzyloxy)-4-chlorophenyl)-1,2,4-thiadiazol-5-yl) methanol

HRID 453120Notes

Reaction equation

HRID 453120 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[C:16]1[N:20]=[C:19]([C:21](OCC)=[O:22])[S:18][N:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CCO>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[C:16]1[N:20]=[C:19]([CH2:21][OH:22])[S:18][N:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59549530Ethyl 3-(2-(benzyloxy)-4-chlorophenyl)-1,2,4-thiadiazole-5-carboxylate

Product 1

HCID 59549526(3-(2-(Benzyloxy)-4-chlorophenyl)-1,2,4-thiadiazol-5-yl) methanolYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 3-(2-(benzyloxy)-4-chlorophenyl)-1,2,4-thiadiazole-5-carboxylate (0.45 g, 1.20 mmol) in EtOH (25 ml) was added sodium borohydride (0.113 g, 3.0 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 to get the desired product (0.35 g, 88%) 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

Sources & evidence

ORD record
ord-519cdc53457d421b8a171c54ab7687a8
Source dataset
uspto-grants-2013_07
Patent number
US08492414B2

Reaction notes

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