Triphenylphosphine → Methyl 2-((1-(((tert-butyl(dimethyl)silyl)oxy)methyl)prop-2-enyl)oxy)-6-hydroxybenzoate

HRID 1375671

Reaktionsgleichung

Reaktionsgleichung von HRID 1375671
[Si:1]([O:8][CH2:9][CH:10]([OH:13])[CH:11]=[CH2:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:14][O:15][C:16](=[O:25])[C:17]1[C:22]([OH:23])=[CH:21][CH:20]=[CH:19][C:18]=1O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>>[Si:1]([O:8][CH2:9][CH:10]([O:13][C:18]1[CH:19]=[CH:20][CH:21]=[C:22]([OH:23])[C:17]=1[C:16]([O:15][CH3:14])=[O:25])[CH:11]=[CH2:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Komponenten

5

Edukt 4

HCID 11776TriphenylphosphineHCID 519869Methyl 2,6-dihydroxybenzoateHCID 5462977Diethyl azodicarboxylateHCID 109105951-[(Tert-butyldimethylsilyl)oxy]but-3-en-2-ol

Produkt 1

HCID 69507994Methyl 2-((1-(((tert-butyl(dimethyl)silyl)oxy)methyl)prop-2-enyl)oxy)-6-hydroxybenzoateAusbeute 24 %

Versuchsvorschrift

A solution of alcohol from Example 16A (2.65 g, 13.1 mmol), methyl-2,6-dihydroxybenzoate (3.51 g, 20.9 mmol), PPh3 (3.34 g, 15.7 mmol), and TBF (20 mL) was cooled to 0° C. Diethylazodicarboxylate (2.51 g, 14.4 mmol) was added. The reaction was allowed to warm to room temperature and stir for 16 hours. The titled product (1.11 g, 24%) was obtained following silica gel column chromatography (10% ethyl acetate in hexanes).

Quellen und Nachweise

ORD-Eintrag
ord-941dc56f440941d9aba0da985491fcfd
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07169797B2

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