Triphenylphosphine → Tert-butyl 4-tert-butyl-3-(cyclopropylmethoxy)phenyl carbonate

HRID 1350866Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1350866
[C:1](=[O:19])([O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])=[C:10]([OH:18])[CH:9]=1)[O:2][C:3]([CH3:6])([CH3:5])[CH3:4].[CH:20]1([CH2:23]O)[CH2:22][CH2:21]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>>[C:1](=[O:19])([O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])=[C:10]([O:18][CH2:23][CH:20]2[CH2:22][CH2:21]2)[CH:9]=1)[O:2][C:3]([CH3:6])([CH3:5])[CH3:4]

Komponenten

5

Edukt 4

HCID 11776TriphenylphosphineHCID 75644CyclopropanemethanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 15482845Tert-butyl 4-tert-butyl-3-hydroxyphenyl carbonate

Produkt 1

HCID 21097538Tert-butyl 4-tert-butyl-3-(cyclopropylmethoxy)phenyl carbonateAusbeute 79,1 %

Versuchsvorschrift

Tert-butyl 4-tert-butyl-3-hydroxyphenyl carbonate (1.5 g, 5.6 mmol), cyclopropylmethanol (0.5 mL, 6.2 mmol), triphenylphosphine (1.6 g, 6.2 mmol) and diethyl azodicarboxylate (DEAD) (1.0 mL, 6.2 mmol) were treated in the same procedure described in Example 31(a). The crude residue was applied to a silica gel chromatography column and eluted with a volume mixture of hexane and ethyl acetate (19/1 to 9/1) to furnish 1.42 g (79% yield) of the title compound as a yellow oil.

Aufarbeitung

  1. washeluted with a volume mixture of hexane and ethyl acetate (19/1 to 9/1)

Quellen und Nachweise

ORD-Eintrag
ord-de5c770a597c41a290d781575f944ef7
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07214824B2

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