Water → Ethyl 2,6-Diisopropyl-4-(4-fluorophenyl)-3-hydroxymethylpyridine-5-carboxylate

HRID 324790Notes

Reaction equation

[CH:1]([C:4]1[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:8]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[C:7]([C:22](OCC)=[O:23])=[C:6]([CH:27]([CH3:29])[CH3:28])[N:5]=1)([CH3:3])[CH3:2].O>O1CCCC1>[CH:27]([C:6]1[C:7]([CH2:22][OH:23])=[C:8]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:4]([CH:1]([CH3:2])[CH3:3])[N:5]=1)([CH3:29])[CH3:28]

Participants

Conditions

Temperature: 0 °C

Procedure

257 ml (0.9 mol) of a 3.5 molar solution of sodium-bis-(2-methoxy-ethoxy)dihydroaluminate is steadily added by drops under nitrogen to a solution of 120 g (0.3 mol) of the compound from Example VIII in 800 ml of dried tetrahydrofuran at room temperature, and the mixture is subsequently stirred for 5 h. After cooling to 0° C., 500 ml of water is carefully added by drops, the phases are separated, and the aqueous phase is extracted three times with 250 ml ethyl acetate each time. The combined organic phases are washed with saturated sodium chloride solution, dried over magnesium sulfate, and evaporated in a vacuum. The residue is mixed with petroleum ether, drawn off by suction, and dried in a desiccator.

Workup

customthe phases are separated
extractionthe aqueous phase is extracted three times with 250 ml ethyl acetate each time
washThe combined organic phases are washed with saturated sodium chloride solution
dry with materialdried over magnesium sulfate
customevaporated in a vacuum
additionThe residue is mixed with petroleum ether
customdried in a desiccator

Sources & evidence

ORD record: ord-2d2fe669d3b44e6b9af94d66818dcb18
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06218431B1

Reaction notes

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