Aluminium lithium hydride → HCID 22909714, compound

HRID 1379102Notes

Reaction equation

HRID 1379102 reaction equation
C([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:16]([C:17]3[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=3)=[CH:15][C:14]([C:27]([F:30])([F:29])[F:28])=[N:13]2)=[CH:8][CH:7]=1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[OH:3][CH2:4][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:16]([C:17]3[CH:18]=[CH:19][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:21][CH:22]=3)=[CH:15][C:14]([C:27]([F:28])([F:29])[F:30])=[N:13]2)=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22909667HCID 22909667, compound

Product 1

HCID 22909714HCID 22909714, compoundYield 59.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 1-[4-(ethoxycarbonyl)phenyl]-5-[4-(methylsulfonyl)phenyl]-3-(trifluoromethyl)pyrazole (2.4 g) and lithium aluminum hydride (0.25 g) in tetrahydrofuran (20 ml) was stirred at 55° C. for 2 hours. The reaction was quenched with methanol and water, and the mixture was filtered. The filtrate was concentrated and the residue was dissolved in a mixture of ethyl acetate and tetrahydrofuran. The solution was washed with water, dried, and evaporated. The residue was purified by column chromatography on silica gel eluting with a mixture of chloroform and methanol (20:1) to give a white powder of 1-[4-(hydroxymethyl)phenyl]-5-[4-(methylsulfonyl)phenyl]-3-(trifluoromethyl)pyrazole (1.3 g).

Workup

  1. customThe reaction was quenched with methanol and water
  2. filtrationthe mixture was filtered
  3. concentrationThe filtrate was concentrated
  4. dissolutionthe residue was dissolved in a mixture of ethyl acetate and tetrahydrofuran
  5. washThe solution was washed with water
  6. customdried
  7. customevaporated
  8. customThe residue was purified by column chromatography on silica gel eluting with a mixture of chloroform and methanol (20:1)

Sources & evidence

ORD record
ord-57e753cb96a24949b9c1ebbc24e1027b
Source dataset
uspto-grants-1997_09
Patent number
US05670533

Reaction notes

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