Aluminium lithium hydride → HCID 57941392, compound

HRID 1437862Notes

Reaction equation

HRID 1437862 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([C:12]1[C:13]([C:36]([F:39])([F:38])[F:37])=[N:14][N:15]([C:17]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:16]=1)=O)C>O1CCCC1>[F:39][C:36]([F:37])([F:38])[C:13]1[C:12]([CH2:10][OH:9])=[CH:16][N:15]([C:17]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:14]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57941469HCID 57941469, compound

Product 1

HCID 57941392HCID 57941392, compoundYield 108.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-12.5 °C

Procedure

A solution of lithium aluminum hydride in THF (1.0 M; 1.6 mL, 1.6 mmol) was added to a cooled (˜−15° C.) solution of 3-trifluoromethyl-1-trityl-1H-pyrazole-4-carboxylic acid ethyl ester (0.64 g, 1.4 mmol) in anhydrous tetrahydrofuran (15 mL). The solution was stirred at −10 to −15° C. for 45 min and then quenched at −10° C. with a solution of Rochelle's salt (2 mL). The mixture was stirred for 10 min and then the cooling bath was removed. Ethyl acetate (25 mL) was added and the mixture was stirred for 30 min, then it was filtered and the filter cake was washed with ethyl acetate. The filtrate was dried (magnesium sulfate), filtered, evaporated, and held under high vacuum over the weekend to give (3-trifluoromethyl-1-trityl-1H-pyrazol-4-yl)-methanol (0.62 g, quantitative) as a tacky white oil.

Workup

  1. customquenched at −10° C. with a solution of Rochelle's salt (2 mL)
  2. stirringThe mixture was stirred for 10 min
  3. customthe cooling bath was removed
  4. additionEthyl acetate (25 mL) was added
  5. stirringthe mixture was stirred for 30 min
  6. filtrationit was filtered
  7. washthe filter cake was washed with ethyl acetate
  8. dry with materialThe filtrate was dried (magnesium sulfate)
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-4ad4e29ac8504048887c72a484ada256
Source dataset
uspto-grants-2009_11
Patent number
US07622492B2

Reaction notes

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