Benzyl Alcohol → (1-Phenyl-cyclohexyl)-carbamic acid benzyl ester

HRID 2235198Notizen

Reaktionsgleichung

[C:1]1([C:7]2(C(O)=O)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([N:18]([CH2:21]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:30])C=CC=CC=1.[CH2:40]([OH:47])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>C1C=CC=CC=1>[CH2:40]([O:47][C:21](=[O:30])[NH:18][C:7]1([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

Dissolve 1-phenyl-cyclohexanecarboxylic acid (5.0 g, 24.48 mmol) in benzene (200 mL). Add triethylamine (2.45 g, 24.48 mmol), diphenylphosphoryl azide (6.74 g, 24.48 mmol), and benzyl alcohol (3.97 g, 36.72 mmol) under nitrogen. Stir and heat the reaction mixture to 80° C. Continue to heat the reaction at 80° C. for 8 hours, then cool to room temperature. Add water (250 mL), and extract the aqueous layer with ethyl acetate (3×300 mL). Combine the organic layers and dry with Na2SO4, filter, concentrate and purify by flash column chromatography (silica gel, 5-25% of EtOAc/Hexane) to give 2.87 g (38%) of the title compound as a colorless oil.

Aufarbeitung

temperatureto heat
customthe reaction at 80° C. for 8 hours
temperaturecool to room temperature
extractionAdd water (250 mL), and extract the aqueous layer with ethyl acetate (3×300 mL)
dry with materialCombine the organic layers and dry with Na2SO4
filtrationfilter
concentrationconcentrate
custompurify by flash column chromatography (silica gel, 5-25% of EtOAc/Hexane)

Quellen und Nachweise

ORD-Eintrag: ord-2fbe188cdd314f84b899a53aec685cf6
Quelldatensatz: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07713979B2

Notizen zur Reaktion

Wird geladen…