Acetovanillone → 1-(3-Methoxy-4-((6-methoxypyridin-3-yl)methoxy)phenyl)ethan-1-one

HRID 706507Notes

Reaction equation

HRID 706507 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[O:11][CH3:12].C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:21][C:22]1[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[N:26][CH:27]=1>C(#N)C.O>[CH3:12][O:11][C:3]1[CH:4]=[C:5]([C:8](=[O:10])[CH3:9])[CH:6]=[CH:7][C:2]=1[O:1][CH2:21][C:22]1[CH:27]=[N:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 2214AcetovanilloneHCID 11430Potassium CarbonateHCID 534389575-(Chloromethyl)-2-methoxypyridine hydrochloride

Product 1

HCID 1181140911-(3-Methoxy-4-((6-methoxypyridin-3-yl)methoxy)phenyl)ethan-1-oneYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred suspension of 1-(4-hydroxy-3-methoxyphenyl)ethan-1-one (3.96 g, 23.82 mmol) and potassium carbonate (13.17 g, 95.29 mmol) in acetonitrile (75 mL) was added 5-(chloromethyl)-2-methoxypyridine hydrochloride (4.85 g, 25.01 mmol). After 2 h, the mixture was diluted with water (150 mL) and extracted with dichloromethane (3×100 mL). The combined organic phases were dried over magnesium sulfate, filtered, and concentrated to provide a yellow oil. Trituration of the crude material with hexanes afforded 5.48 g (85%) of 1-(3-methoxy-4-((6-methoxypyridin-3-yl)methoxy)phenyl)ethan-1-one as a white solid.

Workup

  1. extractionextracted with dichloromethane (3×100 mL)
  2. dry with materialThe combined organic phases were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto provide a yellow oil

Sources & evidence

ORD record
ord-21ad074667c8498299a646d003a3f999
Source dataset
uspto-grants-2015_11
Patent number
US09174986B2

Reaction notes

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