tert-Butanol → 2-((1S)-1,2-dihydroxyethyl)-4,5-diphenyloxazole
Reaction equation
CC[C@@H]1[C@@H]2C[C@H]([C@@H](OC3C4C(=CC=CC=4)C(O[C@@H](C4C=CN=C5C=4C=C(OC)C=C5)[C@@H]4N5C[C@H](CC)[C@@H](CC5)C4)=NN=3)C3C=CN=C4C=3C=C([O:22]C)C=C4)N(CC2)C1.CS(N)(=O)=O.C(C1[O:67][C:68]([C:77]2[CH:82]=[CH:81][CH:80]=[CH:79][CH:78]=2)=[C:69]([C:71]2[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=2)[N:70]=1)=C.S([O-])([O-])=O.[Na+].[Na+].[C:89]([OH:93])([CH3:92])([CH3:91])C>O>[OH:93][C@H:89]([C:92]1[O:67][C:68]([C:77]2[CH:82]=[CH:81][CH:80]=[CH:79][CH:78]=2)=[C:69]([C:71]2[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=2)[N:70]=1)[CH2:91][OH:22]Participants
7
Procedure
A solution of AD-mix-β (trade name, Aldrich) (114 g) in a mixture of t-butyl alcohol (400 ml) and water (400 ml) was stirred for 1 hour, and then methanesulfonamide (7.6 g) and 2-vinyl-4,5-diphenyloxazole (20 g) was added to the solution at 0° C. After being stirred for 8 hours at the same temperature, sodium sulfite (50 g) was added, and the mixture was stirred for 30 minutes. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with 1N-HCl solution, sat. NaHCO3, and brine, dried over MgSO4, and evaporated in vacuo. The residue was purified by trituration with hexane-ether to afford 2-((1S)-1,2-dihydroxyethyl)-4,5-diphenyloxazole (21 g).
Workup
- additionwas added
- stirringthe mixture was stirred for 30 minutes
- customThe mixture was partitioned between ethyl acetate and water
- washThe organic layer was washed with 1N-HCl solution, sat. NaHCO3, and brine
- dry with materialdried over MgSO4
- customevaporated in vacuo
- customThe residue was purified by trituration with hexane-ether
Sources & evidence
- ORD record
- ord-8d279bcf916f4d24afaf1dea6c42ad33
- Source dataset
- uspto-grants-2001_10
- Patent number
- US06300344B1
Reaction notes
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