Acetic Acid → (S)-(+)-Glycidyl butyrate

HRID 392545

Reaktionsgleichung

Reaktionsgleichung von HRID 392545
[C:1]([O:6][CH2:7][CH:8]1[O:10][CH2:9]1)(=[O:5])[CH2:2][CH2:3][CH3:4].CC(O)=O.O.C(OCC1C=CC=CC=1)[C@@H]1OC1>C1COCC1>[C:1]([O:6][CH2:7][C@H:8]1[O:10][CH2:9]1)(=[O:5])[CH2:2][CH2:3][CH3:4]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 962WaterHCID 137606Glycidyl butyrateHCID 159746(-)-Benzyl (R)-glycidyl ether

Produkt 1

HCID 6999819(S)-(+)-Glycidyl butyrateAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Using the (R,R)-(salen)Co(II) precatalyst of 1 (91 mg, 0.15 mmol, 0.005equiv), (+/−)-glycidyl butyrate (4.32 g, 30.0 mmol), AcOH (32 mL, 0.6 mnmol, 0.02 equiv), 0.3 mL THF, and H2O (297 mL, 16.5 mmol, 0.55 equiv) and a procedure analogous to the one outlined for 5b, (S)-glycidyl butyrate 5d (1.90 g, 13.2 mmol, 44%) was obtained as a clear oil by vacuum distillation of the reaction mixture (30° C., 0.5 torr). The product was determined to be >99% ee by conversion to and analysis of the 2-napthylsulfide (obtained by ring opening with 2-napthalenethiol in methanol using 1 equiv TEA at 0° C.; Chiralcel OD, 97:3 hexanes:EtOH, 1 mL/min, 260 mn).

Quellen und Nachweise

ORD-Eintrag
ord-6d85519c2fdc4c0d8339146ac19faa4b
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06800766B2

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