Lithium Hydroxide → {1-[4-(Pentafluoro-lambda6-sulfanyl)phenyl]-1H-tetrazol-5-yl}methanol

HRID 517730Notes

Reaction equation

HRID 517730 reaction equation
[OH-].[Li+].C([O:6][CH2:7][C:8]1[N:12]([C:13]2[CH:18]=[CH:17][C:16]([S:19]([F:24])([F:23])([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)[N:11]=[N:10][N:9]=1)(=O)C>C(O)C.O>[F:24][S:19]([F:20])([F:21])([F:22])([F:23])[C:16]1[CH:17]=[CH:18][C:13]([N:12]2[C:8]([CH2:7][OH:6])=[N:9][N:10]=[N:11]2)=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86691878{1-[4-(pentafluoro-lambda6-sulfanyl)phenyl]-1H-tetrazol-5-yl}methyl acetate2×

Product 1

HCID 86691877{1-[4-(Pentafluoro-lambda6-sulfanyl)phenyl]-1H-tetrazol-5-yl}methanolYield 86.1%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

Lithium hydroxide (553 mg, 22.2 mmol) was added to a solution of {1-[4-(pentafluoro-λ6-sulfanyl)phenyl]-1H-tetrazol-5-yl}methyl acetate (Intermediate 43, 5.30 g, 15.3 mmol) in ethanol:water (2:1), at 0° C. The reaction mixture was stirred for 3 hr at room temperature. The solvent was removed by under reduced pressure and the residue was diluted with DCM, washed with ice-water, saturated aq NaHCO3 and brine solution, dried over anhydrous Na2SO4, and concentrated under reduced pressure to give the crude product. This was purified by column chromatography (100-200 mesh silica gel), eluting with 30%-40% EtOAc/pet-ether gave the title compound (3.98 g).

Workup

  1. customThe solvent was removed by under reduced pressure
  2. additionthe residue was diluted with DCM
  3. washwashed with ice-water, saturated aq NaHCO3 and brine solution
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customto give the crude product
  7. customThis was purified by column chromatography (100-200 mesh silica gel)
  8. washeluting with 30%-40% EtOAc/pet-ether

Sources & evidence

ORD record
ord-bc4c72278e9c412181cee5b457e8b4ff
Source dataset
uspto-grants-2015_08
Patent number
US09115132B2

Reaction notes

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