Triphenylphosphine → [4-(Tetrahydro-pyran-4-yloxy)-naphthalen-1-yl]-carbamic acid tert-butyl ester

HRID 23533

Reaktionsgleichung

C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[C:32]([O:36][C:37](=[O:50])[NH:38][C:39]1[C:48]2[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=2)[C:42]([OH:49])=[CH:41][CH:40]=1)([CH3:35])([CH3:34])[CH3:33].[O:51]1[CH2:56][CH2:55][CH:54](O)[CH2:53][CH2:52]1>C1COCC1>[C:32]([O:36][C:37](=[O:50])[NH:38][C:39]1[C:48]2[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=2)[C:42]([O:49][CH:54]2[CH2:55][CH2:56][O:51][CH2:52][CH2:53]2)=[CH:41][CH:40]=1)([CH3:35])([CH3:33])[CH3:34]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

Triphenylphosphine (2.8 g, 10.8 mmol) was dissolved in THF (5 mL) and cooled to 0° C. To this colorless solution diethylazodicarboxylate (1.9 grams, 10.8 mmol) was added dropwise to afford an orange solution. After 15 min at 0° C., a copious precipitate had formed. 4-Hydroxy-naphthalen-1-yl-carbamic acid tert-butyl ester (934 mg, 3.6 mmol) and tetrahydro-4H-pyran-4-ol (552 mg, 5.4 mmol) were then added in one portion as a solution in 2 mL of THF. The purple suspension was stirred at 0° C. for one h then at room temperature for 48 h. The solvent was then evaporated and chromatographed on silica gel (40% EtOAc-hexanes) to provide 680 mg (55%) of [4-(tetrahydro-pyran-4-yloxy)-naphthalen-1-yl]-carbamic acid tert-butyl ester as a purple solid.

Aufarbeitung

customto afford an orange solution
customa copious precipitate had formed
waitat room temperature for 48 h
customThe solvent was then evaporated
customchromatographed on silica gel (40% EtOAc-hexanes)

Quellen und Nachweise

ORD-Eintrag: ord-3ce72494a05e4cd89083727714415d7a
Quelldatensatz: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06852717B2

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