Water → [4-(4-Fluorophenyl)-5-(methoxymethyl)-2,6-di(propan-2-yl)pyridin-3-yl]methanol

HRID 1681254Notes

Reaction equation

[CH:1]([C:4]1[C:9]([C:10](OCC)=[O:11])=[C:8]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[C:7]([CH2:22][O:23][CH3:24])=[C:6]([CH:25]([CH3:27])[CH3:26])[N:5]=1)([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[K+]>O1CCCC1>[CH:1]([C:4]1[C:9]([CH2:10][OH:11])=[C:8]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[C:7]([CH2:22][O:23][CH3:24])=[C:6]([CH:25]([CH3:27])[CH3:26])[N:5]=1)([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

2.85 g (7.6 mmol) of the compound from Example 59 dissolved in 30 ml of absolute tetrahydrofuran are added dropwise under a nitrogen atmosphere to 0.5 g (13.2 mmol) of lithium aluminum hydride in 20 ml of absolute tetrahydrofuran at 60° C. The mixture is heated to reflux for 1 hour, subsequently cooled to 0° C. and 1.5 ml of water and 0.3 ml of 15% strength potassium hydroxide solution are cautiously added dropwise. The solution is filtered from the deposited precipitate with suction and the latter is boiled several times with ether. The combined phases are dried over magnesium sulphate and concentrated in vacuo. The residue is chromatographed on a column (silica gel 70-230 mesh, using ethyl acetate/petroleum ether 1:9).

Workup

temperatureThe mixture is heated
temperatureto reflux for 1 hour
filtrationThe solution is filtered from the deposited precipitate with suction
dry with materialThe combined phases are dried over magnesium sulphate
concentrationconcentrated in vacuo
customThe residue is chromatographed on a column (silica gel 70-230 mesh, using ethyl acetate/petroleum ether 1:9)

Sources & evidence

ORD record: ord-a33514f2a859402eab2fdc17e17f6619
Source dataset: uspto-grants-1992_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05169857

Reaction notes

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