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

HRID 395416Notes

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-64bb0663e2c0480593b178f712623a2f
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06605620B1

Reaction notes

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