Hydrochloric Acid → 2-(5-Methyl-2-phenyl-1,3-oxazol-4-yl)ethyl methanesulfonate
Reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][OH:15].[CH3:16][S:17](Cl)(=[O:19])=[O:18].C(N(CC)CC)C.Cl>C1(C)C=CC=CC=1>[CH3:16][S:17]([O:15][CH2:14][CH2:13][C:3]1[N:4]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[O:6][C:2]=1[CH3:1])(=[O:19])=[O:18]Participants
Procedure
2-(5-Methyl-2-phenyl-4-oxazolyl)ethanol (compound [6]; 108.6 g) obtained in Example 3 was dissolved in toluene (600 mL), and methanesulfonyl chloride (45.4 mL) was added, which was followed by stirring under ice-cooling. To this solution was added dropwise triethylamine (81.7 mL) under ice-cooling. After stirring for 1 hr, toluene (1 L) was added and 1N hydrochloric acid (1 L) was added for partitioning. The aqueous layer was extracted again with toluene (0.5 L). The combined organic layers were washed successively with water (1 L), saturated sodium hydrogencarbonate solution (1 L) and saturated brine (1 L), and dried over anhydrous magnesium sulfate. The desiccant was filtered off and the filtrate was concentrated under reduced pressure to give the title compound (compound [7]; 150 g, yield 100%) as crystals.
Workup
- temperaturecooling
- temperaturecooling
- stirringAfter stirring for 1 hr
- customfor partitioning
- extractionThe aqueous layer was extracted again with toluene (0.5 L)
- washThe combined organic layers were washed successively with water (1 L), saturated sodium hydrogencarbonate solution (1 L) and saturated brine (1 L)
- dry with materialdried over anhydrous magnesium sulfate
- filtrationThe desiccant was filtered off
- concentrationthe filtrate was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-3c9cf212c1c745ac917403cabfac48b9
- Source dataset
- uspto-grants-2006_02
- Patent number
- US06995271B2
Reaction notes
Loading…