Potassium Sodium Tartrate → 5-(3-Hydroxypropyl)-1-methyl-2-ethylimidazole
Reaction equation
[CH3:1][N:2]1[C:6]([CH2:7][CH2:8][C:9](OCC)=[O:10])=[CH:5][N:4]=[C:3]1[CH2:14][CH3:15].[H-].[H-].[H-].[H-].[Li+].[Al+3].[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1COCC1>[OH:10][CH2:9][CH2:8][CH2:7][C:6]1[N:2]([CH3:1])[C:3]([CH2:14][CH3:15])=[N:4][CH:5]=1Participants
Conditions
- Temperature
- 0 °C
Procedure
To a cooled (0° C.) solution of ethyl 3-(1-methyl-2-ethylimidazol-5-yl)propionate (1.75 g, 8:33 mmol) in 30 ml of THF was added 4.6 ml (4.6 mmol) of 1M LAH solution in THF at 0° C. After stirring at 0° C. for 15 min, the mixture was allowed to warm and stirred at 20° C. for 0.7 h. Rochelle salt solution (equiv) was added and the mixture was stirred for 20 min. The aqueous mixture was extracted with methylene chloride and filtered. The organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by chromatography on silica (10 cm column, methylene chloride/methanol, 6/1-6/1) followed by recrystallization from acetonitrile/ether and methylene chloride/hexane to afford 1.268 g (90%) of 5-(3-hydroxypropyl)-1-methyl-2-ethylimidazole, as a white solid, m.p. 69°-71° C.
Workup
- temperatureto warm
- stirringstirred at 20° C. for 0.7 h
- stirringthe mixture was stirred for 20 min
- extractionThe aqueous mixture was extracted with methylene chloride
- filtrationfiltered
- dry with materialThe organic layer was dried over sodium sulfate
- concentrationconcentrated in vacuo
- customThe residue was purified by chromatography on silica (10 cm column, methylene chloride/methanol, 6/1-6/1)
- customfollowed by recrystallization from acetonitrile/ether and methylene chloride/hexane
Sources & evidence
- ORD record
- ord-e533b65814c14ae8b03810c2d15101f1
- Source dataset
- uspto-grants-1998_12
- Patent number
- US05846986
Reaction notes
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