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

HRID 984145Notes

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 (24.57 g) was dissolved in dry THF (200 mL), and to the solution lithium aluminum hydride (2.94 g) was added at 0° C. under an argon atmosphere. The mixture was stirred at 0° C. for 1 hour as it is. 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 evaporated, and the reultant crude crystals were recrystalized from ethyl acetate-hexane to give the title compound.

Workup

filtrationthe reaction mixture was filtered through celite
customThe filtrate was evaporated
customthe reultant crude crystals were recrystalized from ethyl acetate-hexane

Sources & evidence

ORD record: ord-759de1022d9a41f78a2872fb3591724e
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06867221B2

Reaction notes

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