Water → HCID 13478150, compound

HRID 2350916Notes

Reaction equation

HRID 2350916 reaction equation
[CH3:1][C:2]([C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1)([CH3:5])[CH2:3][OH:4].[H-].[Na+].I[CH3:15].O>CN(C)C=O>[CH3:5][C:2]([C:6]1[CH:7]=[CH:8][N:9]=[CH:10][CH:11]=1)([CH3:1])[CH2:3][O:4][CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 134781392-Methyl-2-(pyridin-4-yl)propan-1-ol

Product 1

HCID 13478150HCID 13478150, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
-20 °C

Procedure

A solution of 4-(1,1-dimethyl-2-hydroxyethyl)pyridine (15 g) in dry dimethylformamide (150 ml) was treated with sodium hydride (80% oil dispersion; 3.3 g) under nitrogen at 0° C. with stirring. After 15 minutes at 0° C., this mixture was cooled to -20° C., and a solution of iodomethane (7.4 ml) in dry dimethylformamide (50 ml) was added dropwise during 5 minutes. The mixture which changed from a white to an orange precipitate was allowed to slowly warm to ambient temperature, and stirred overnight under nitrogen. After pouring into excess water, the mixture was extracted with three portions of dichloromethane. The extract was washed with water twice, dried over anhydrous magnesium sulphate and evaporated in vacuo to give a dark oil after further evaporation of added toluene. This oil was chromatographed on silica gel (Merck; 0.04-0.063 mm) under medium pressure using a mixture of dichloromethane and ethyl acetate (2:1) as solvent to give 4-(1,1-dimethyl-2-methoxyethyl)pyridine (11.0 g) as a brown oil.

Workup

  1. temperatureto slowly warm to ambient temperature
  2. stirringstirred overnight under nitrogen
  3. extractionthe mixture was extracted with three portions of dichloromethane
  4. washThe extract was washed with water twice
  5. dry with materialdried over anhydrous magnesium sulphate
  6. customevaporated in vacuo
  7. customto give a dark oil
  8. customafter further evaporation of added toluene
  9. customThis oil was chromatographed on silica gel (Merck; 0.04-0.063 mm) under medium pressure
  10. additiona mixture of dichloromethane and ethyl acetate (2:1) as solvent

Sources & evidence

ORD record
ord-518ebd60b45c4e5d88d6251d737fdf72
Source dataset
uspto-grants-1989_10
Patent number
US04871748

Reaction notes

Loading…