Lithium Hydroxide → HCID 66654249, compound

HRID 517739Notes

Reaction equation

HRID 517739 reaction equation
C([O:4][CH2:5][C:6]1[N:10]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[C:13]([O:19][C:20]([F:23])([F:22])[F:21])[CH:12]=2)[N:9]=[N:8][N:7]=1)(=O)C.[OH-].[Li+]>CO.C1COCC1.O>[OH:4][CH2:5][C:6]1[N:10]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[C:13]([O:19][C:20]([F:23])([F:22])[F:21])[CH:12]=2)[N:9]=[N:8][N:7]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 66655178HCID 66655178, compound2×

Product 1

HCID 66654249HCID 66654249, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Conditions

Temperature
0 °C

Procedure

(1-{4-Cyano-3-[(trifluoromethyl)oxy]phenyl}-1H-tetrazol-5-yl)methyl acetate (Intermediate 53, 7.0 g, 21.4 mmol) was dissolved in MeOH:THF:H2O (1:2:1) and the solution was cooled to 0° C. Lithium hydroxide (770 mg, 32.2 mmol) was added at 0° C. The reaction was slowly allowed to reach room temperature and stirred for 3 hr. The solvent was removed under reduced pressure. The residue was diluted with DCM, and washed with ice-cooled 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% EtOAc/pet ether to give the title compound (3.50 g).

Workup

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

Sources & evidence

ORD record
ord-a5866a3c79864ff48270f0d8e7915e9a
Source dataset
uspto-grants-2015_08
Patent number
US09115132B2

Reaction notes

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