tert-Butanol → 2-((1S)-1,2-dihydroxyethyl)-4,5-diphenyloxazole

HRID 380121Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 380121
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]

Komponenten

7

Edukt 5

HCID 6386tert-ButanolHCID 24437Sodium SulfiteHCID 72879MethanesulfonamideHCID 108902322-Vinyl-4,5-diphenyloxazoleHCID 112172021,4-Bis(dihydroquinidine)phthalazine

Produkt 1

HCID 569827262-((1S)-1,2-dihydroxyethyl)-4,5-diphenyloxazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  1. additionwas added
  2. stirringthe mixture was stirred for 30 minutes
  3. customThe mixture was partitioned between ethyl acetate and water
  4. washThe organic layer was washed with 1N-HCl solution, sat. NaHCO3, and brine
  5. dry with materialdried over MgSO4
  6. customevaporated in vacuo
  7. customThe residue was purified by trituration with hexane-ether

Quellen und Nachweise

ORD-Eintrag
ord-8d279bcf916f4d24afaf1dea6c42ad33
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06300344B1

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