Hydrochloric Acid → Carbonic acid 4-nitro-phenyl ester (R)-1-phenyl-ethyl ester

HRID 423950

Reaktionsgleichung

[C:1]1([C@H:7]([OH:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.CC1CCCO1.Cl[C:23]([O:25][C:26]1[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=1)=[O:24].Cl>O>[C:1]1([C@H:7]([O:9][C:23](=[O:24])[O:25][C:26]2[CH:27]=[CH:28][C:29]([N+:32]([O-:34])=[O:33])=[CH:30][CH:31]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

A mixture of (R)-1-phenyl-ethanol (60.6 g, 0.496 mol), pyridine (42.5 mL, 0.526 mol) and 2-methyl-tetrahydrofuran (600 mL) was cooled to 0° C. and p-nitrophenyl chloroformate (100 g, 0.496 mol) was added over 15 min keeping the internal temperature below 5° C. The reaction mixture was warmed to room temperature and stirred for 2 h. To the reaction mixture was added 1.0 M HCl in water (300 mL). Layers were separated. The organic layer was washed with 1N HCl (300 mL) and brine (300 mL), filtered, concentrated to dryness by rotary evaporation, and dried under vacuum to give the title compound (140 g) as a clear yellow oil.

Aufarbeitung

customthe internal temperature below 5° C
temperatureThe reaction mixture was warmed to room temperature
customLayers were separated
washThe organic layer was washed with 1N HCl (300 mL) and brine (300 mL)
filtrationfiltered
concentrationconcentrated to dryness by rotary evaporation
customdried under vacuum

Quellen und Nachweise

ORD-Eintrag: ord-da4a8c0ee518429692089bb3943c4831
Quelldatensatz: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08101794B2

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