Aluminium lithium hydride → (3-(5,5-Dimethylcyclopent-1-enyl)-4-(5-fluoro-2-methoxypyridin-4-yl)phenyl)methanol

HRID 404350Notes

Reaction equation

[CH3:1][C:2]1([CH3:26])[C:6]([C:7]2[CH:8]=[C:9]([CH:14]=[CH:15][C:16]=2[C:17]2[C:22]([F:23])=[CH:21][N:20]=[C:19]([O:24][CH3:25])[CH:18]=2)[C:10](OC)=[O:11])=[CH:5][CH2:4][CH2:3]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][C:2]1([CH3:26])[C:6]([C:7]2[CH:8]=[C:9]([CH2:10][OH:11])[CH:14]=[CH:15][C:16]=2[C:17]2[C:22]([F:23])=[CH:21][N:20]=[C:19]([O:24][CH3:25])[CH:18]=2)=[CH:5][CH2:4][CH2:3]1

Participants

Conditions

Temperature: 0 °C

Procedure

To methyl 3-(5,5-dimethylcyclopent-1-enyl)-4-(5-fluoro-2-methoxypyridin-4-yl)benzoate T19.2 (295 mg, 830 μmol) was added THF. The mixture was cooled to 0° C., and LAH (1660 μL, 1660 μmol) was added dropwise. The reaction was stirred at room temperature for 1 hour, and was quenched with water and a small amount of Rochelle's salt solution. Purification with silica gel chromatography afforded (3-(5,5-dimethylcyclopent-1-enyl)-4-(5-fluoro-2-methoxypyridin-4-yl)phenyl)methanol T19.3 (201 mg) as an oil (74%).

Workup

customwas quenched with water
customPurification with silica gel chromatography

Sources & evidence

ORD record: ord-b922d375976f477fad2cef8ee9a32c32
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748462B2

Reaction notes

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