Aluminium lithium hydride → HCID 44819039, compound

HRID 1496902Notes

Reaction equation

HRID 1496902 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[F:7][C:8]([F:27])([F:26])[O:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH:20]=[CH:19][C:18]([C:21](OCC)=[O:22])=[N:17]2)=[CH:12][CH:11]=1>CCOCC>[F:27][C:8]([F:7])([F:26])[O:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH:20]=[CH:19][C:18]([CH2:21][OH:22])=[N:17]2)=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 44819036HCID 44819036, compound

Product 1

HCID 44819039HCID 44819039, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

LiAlH4 (0.137 g, 3.61 mmol) was added to a solution of ester 66 (1.081 g, 3.60 mmol) in Et2O (20 mL) at 0° C. and the stirred mixture was warmed to room temperature for 1 h, then cooled to 0° C. and quenched with ice. The mixture was diluted with Et2O (100 mL) and saturated aqueous sodium potassium tartrate (100 mL) and then filtered through Celite. The organic layer was dried and chromatographed on silica gel, eluting with CH2Cl2:EtOAc (95:5), to give {1-[4-(trifluoromethoxy)phenyl]-1H-pyrazol-3-yl}methanol (67) (0.888 g, 96%) as a white solid: mp 53-54° C.; 1H NMR [(CD3)2SO] δ 8.44 (d, J=2.5 Hz, 1H), 7.92 (d, J=8.5 Hz, 2H), 7.48 (d, J=8.5 Hz, 2H), 6.50 (d, J=2.5 Hz, 1H), 5.15 (t, J=5.8 Hz, 1H), 4.51 (d, J=5.8 Hz, 2H). APCI MS m/z 259 [M+H]+.

Workup

  1. temperaturecooled to 0° C.
  2. customquenched with ice
  3. additionThe mixture was diluted with Et2O (100 mL) and saturated aqueous sodium potassium tartrate (100 mL)
  4. filtrationfiltered through Celite
  5. customThe organic layer was dried
  6. customchromatographed on silica gel
  7. washeluting with CH2Cl2:EtOAc (95:5)

Sources & evidence

ORD record
ord-2e72995f360346baa68fad8302fde687
Source dataset
uspto-grants-2015_12
Patent number
US09198913B2

Reaction notes

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