Water → (3-Ethoxy-6-methylpyridin-2-yl)methanol

HRID 1094755

Reaction equation

HRID 1094755 reaction equation
[OH:1][CH2:2][C:3]1[C:8]([OH:9])=[CH:7][CH:6]=[C:5]([CH3:10])[N:4]=1.C([O-])([O-])=O.[K+].[K+].I[CH2:18][CH3:19].O>CN(C=O)C.CCOC(C)=O>[CH2:18]([O:9][C:8]1[C:3]([CH2:2][OH:1])=[N:4][C:5]([CH3:10])=[CH:6][CH:7]=1)[CH3:19]

Participants

7

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 1351283-Hydroxy-2-hydroxymethyl-6-methylpyridine

Product 1

HCID 59363660(3-Ethoxy-6-methylpyridin-2-yl)methanol

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(hydroxymethyl)-6-methyl-3-pyridinol (1.5 g, 10.78 mmol, available from Sigma-Aldrich #144428), K2CO3 (7.45 g, 53.9 mmol) and iodoethane (1.724 ml, 21.56 mmol) were dissolved in DMF (15 ml). The mixture was left stirring at room temperature overnight. Water and EtOAc were added and the two layers were separated. The aqueous one was back-extracted several times with EtOAc. The combined organic phases were washed with brine/ice, dried (Na2SO4), filtered and concentrated under reduced pressure to afford the crude title compound D13 (1.67 g) as a pale yellow solid which was used in the next step without any further purification. MS: (ES/+) m/z: 168 (M+1). C9H13NO2 requires 167. 1H-NMR (400 MHz, CDCl3) δ (ppm): 6.96-7.07 (m, 2 H), 4.71 (s, 2 H), 4.04 (q, 2 H), 2.50 (s, 3 H), 1.43 (t, 3 H).

Workup

  1. waitThe mixture was left
  2. customthe two layers were separated
  3. extractionThe aqueous one was back-extracted several times with EtOAc
  4. washThe combined organic phases were washed with brine/ice
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3cef2e45b2324a4c8cc2de90da3ee8cb
Source dataset
uspto-grants-2012_03
Patent number
US08133908B2

Linked notes

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