Water → 4-Hydroxymethyl-2-(3,4,5-trimethoxyphenyl)pyridine

HRID 1267619Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[CH:14]=[C:15]([CH:21]=[CH:22][N:23]=2)[C:16](OCC)=[O:17])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[OH:17][CH2:16][C:15]1[CH:21]=[CH:22][N:23]=[C:13]([C:5]2[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)[CH:14]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Ethyl 2-(3,4,5-trimethoxyphenyl)isonicotinate (27.70 g) was dissolved in THF (200 mL), and to the solution lithium aluminum hydride (3.31 g) was added at 0° C. under an argon atmosphere, and the mixture was stirred at 0° C. for 1 hour. A small amount of water and then sodium sulfate were added to the reaction mixture, and the reaction mixture was filtered through celite. The filtrate was concentrated under reduced pressure, and the resultant crude crystals were recrystallized from ethyl acetate-hexane to obtain the title compound.

Workup

filtrationthe reaction mixture was filtered through celite
concentrationThe filtrate was concentrated under reduced pressure
customthe resultant crude crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record: ord-e8f99bf5e0a84c658baabc6246f0303c
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06552188B2

Reaction notes

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