Dimethylformamide → 5-(Benzyloxy)-2-methoxy-3-neopentylpyridine

HRID 1049467Notes

Reaction equation

[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([OH:9])=[CH:5][C:4]=1[CH2:10][C:11]([CH3:14])([CH3:13])[CH3:12].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C.[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>O>[CH2:26]([O:9][C:6]1[CH:5]=[C:4]([CH2:10][C:11]([CH3:14])([CH3:13])[CH3:12])[C:3]([O:2][CH3:1])=[N:8][CH:7]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a mixture of 6-methoxy-5-neopentylpyridin-3-ol (2.00 g), potassium carbonate (4.25 g) and DMF (20 mL) was added benzyl bromide (2.40 mL) at room temperature, and the mixture was stirred at 50° C. for 30 min. Water was added to the reaction mixture at room temperature, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give a crude product of the title compound as a colorless oil. This compound was used for the next step without further purification.

Workup

extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with water and saturated brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-45f36894cafc40509767a5d5c88acbca
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382188B2

Reaction notes

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