Aluminium lithium hydride → HCID 14460147, compound

HRID 1720697Notes

Reaction equation

HRID 1720697 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[F:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:17]=[C:16]([CH3:26])[C:15]=2[C:27](OCC)=[O:28])=[CH:10][CH:9]=1>CCOCC>[F:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:17]=[C:16]([CH3:26])[C:15]=2[CH2:27][OH:28])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86749408HCID 86749408, compound

Product 1

HCID 14460147HCID 14460147, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A slurry of LiAlH4 (305 mg, 8.04 mmol) in dry Et2O (30 ml) at 0° C. treated with a solution of 4-(4-fluorophenyl)-2-methyl-6-phenyl-3-pyridinecarboxylic acid, ethyl ester (1.587 gm, 4.73 mmol) in Et2O (4 ml). After 50 minutes, the reaction was quenched and diluted with H2O and the solution was adjusted to neutral pH with 10% HCl. EtOAc was added to dissolve suspended product into the Et2O layer and the mixture was subsequently extracted three times with EtOAc. The combined organic layers were washed with H2O and brine, then dried (Na2SO4), filtered and stripped to give a yellow solid. Recrystallization of the solid from hot hexane/acetone afforded 4-(4-fluorophenyl)-2-methyl-6-phenyl-3-pyridinemethanol (916 mg) as a white solid. An additional 283 mg of 4-(4-fluorophenyl)-2-methyl-6-phenyl-3-pyridinemethanol was obtained by evaporation of the mother liquor followed by recrystallization of the residue from hot hexane/EtOAc, giving a total of 1.199 gm (86%) product.

Workup

  1. customthe reaction was quenched
  2. additiondiluted with H2O
  3. additionEtOAc was added
  4. dissolutionto dissolve
  5. extractionthe mixture was subsequently extracted three times with EtOAc
  6. washThe combined organic layers were washed with H2O and brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customto give a yellow solid
  10. customRecrystallization of the solid from hot hexane/acetone

Sources & evidence

ORD record
ord-bdbd4178447943eabaca114ece89fd23
Source dataset
uspto-grants-1996_04
Patent number
US05506219

Reaction notes

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