Aluminium lithium hydride → HCID 15099539, compound

HRID 1720704Notes

Reaction equation

HRID 1720704 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[F:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:19]([C:20](OCC)=[O:21])=[C:18]([CH:25]([CH3:27])[CH3:26])[CH:17]=[C:16]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:15]=2)=[CH:10][CH:9]=1>C1COCC1>[F:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:19]([CH2:20][OH:21])=[C:18]([CH:25]([CH3:27])[CH3:26])[CH:17]=[C:16]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[N:15]=2)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydride2×HCID 86749411HCID 86749411, compound

Product 1

HCID 15099539HCID 15099539, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a slurry of LiAlH4 (1.457 gm, 38.4 mmol) in dry THF at 0° C. was added a solution of 2-(4-fluorophenyl)-4-(1-methylethyl)-6-phenyl-3-pyridinecarboxylic acid, ethyl ester (3.37 gm, 9.27 mmol) in THF (7 ml). After 4.5 hours, the flask was charged with an additional 0.88 gm LiAlH4 and stirring was continued for 2 more hours. The mixture was quenched with H2O and diluted with H2O and EtOAc. The phases were shaken and separated, and the aqueous layer was extracted again with EtOAc and Et2O. The pooled organic layers were washed with H2O and brine, then dried (Na2SO4), filtered and stripped to give a white solid. The solid was recrystallized from hot EtOAc/hexane to afford 2-(4-fluorophenyl)-4-(1-methylethyl)-6-phenyl-3-pyridinemethanol as white crystals. The mother liquor was stripped and recrystallized again from hot EtOAc/hexane to give a total of 2.684 gm (90%) desired product.

Workup

  1. customThe mixture was quenched with H2O
  2. additiondiluted with H2O and EtOAc
  3. stirringThe phases were shaken
  4. customseparated
  5. extractionthe aqueous layer was extracted again with EtOAc and Et2O
  6. washThe pooled organic layers were washed with H2O and brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customto give a white solid
  10. customThe solid was recrystallized from hot EtOAc/hexane

Sources & evidence

ORD record
ord-3236e65f7c4f477f83f20e6ce05c5a50
Source dataset
uspto-grants-1996_04
Patent number
US05506219

Reaction notes

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