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

HRID 2303348Notes

Reaction equation

HRID 2303348 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[N:23]=[CH:22][CH:21]=[CH:20][C:14]=2C(OCC)=O)[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+].C1C[O:41][CH2:40]C1>>[OH:41][CH2:40][C:20]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

6

Reactant 5

HCID 962WaterHCID 8028TetrahydrofuranHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 22558005HCID 22558005, compound

Product 1

HCID 161259364-Hydroxymethyl-2-(3,4,5-trimethoxyphenyl)pyridine

Conditions

Temperature
0 °C

Procedure

Ethyl 2-(3,4,5-trimethoxyphenyl)nicotinate (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 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 concentrated under reduced pressure, and the resultant crystals were recrystallized from ethyl acetate-hexane to obtain the title compound.

Workup

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

Sources & evidence

ORD record
ord-fb74f9c579644d4489dc89079058dc08
Source dataset
uspto-grants-2002_08
Patent number
US06432957B1

Reaction notes

Loading…