Water → (6-Fluorobenzo[d]thiazol-2-yl)methanol

HRID 1597780Notes

Reaction equation

HRID 1597780 reaction equation
[BH4-].[Li+].[F:3][C:4]1[CH:16]=[CH:15][C:7]2[N:8]=[C:9]([C:11](OC)=[O:12])[S:10][C:6]=2[CH:5]=1.O>CO>[F:3][C:4]1[CH:16]=[CH:15][C:7]2[N:8]=[C:9]([CH2:11][OH:12])[S:10][C:6]=2[CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4148881Lithium borohydride2×HCID 450771692-Benzothiazolecarboxylicacid,6-fluoro-,methylester(9CI)

Product 1

HCID 18932226(6-Fluorobenzo[d]thiazol-2-yl)methanolYield 101.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

16.5 mg of lithium borohydride were added to a solution of 106.1 mg of methyl (6-fluorobenzothiazol-2-yl)formate [prepared as described in step (a) above] in 2.1 ml of methanol cooled in an ice-water bath, and the resulting mixture was stirred at the same temperature for 10 minutes. At the end of this time a further 10 mg of lithium borohydride were added to the reaction mixture which was then stirred at the same temperature for a further 10 minutes. Water was then added to the reaction mixture and the resulting mixture was extracted with ethyl acetate. The resulting extract was washed consecutively with water and an aqueous sodium chloride solution and then dried over sodium sulfate. The solvent was then removed by evaporation under reduced pressure to give 93.1 mg of the title compound as a crude white crystalline solid.

Workup

  1. temperaturecooled in an ice-water bath
  2. stirringwas then stirred at the same temperature for a further 10 minutes
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. extractionThe resulting extract
  5. washwas washed consecutively with water
  6. dry with materialan aqueous sodium chloride solution and then dried over sodium sulfate
  7. customThe solvent was then removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-770ae39f7850477cb4794e07dbf829af
Source dataset
uspto-grants-1998_04
Patent number
US05736487

Reaction notes

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