Reaktion #42192

Reaktionsgleichung

(±)-5-(3-{[tert-butyl(dimethyl)silyl]oxy}-2-hydroxypropyl)indan-4-ol

triphenylphosphine

diethylazodicarboxylate

→

(±)-tert-butyl(dimethyl)(3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-ylmethoxy)silane

Ausbeute 46.0%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture was quenched by the addition of water (10 mL)
2. 2
   Sonstigethe solvent was removed in vacuo
3. 3
   Sonstigeto give a crude solid
4. 4
   SonstigePurification by flash column chromatography (silica, ethyl acetate:hexanes 1:7)

Vorschrift

To a solution of (±)-5-(3-{[tert-butyl(dimethyl)silyl]oxy}-2-hydroxypropyl)indan-4-ol (6.78 g, 21.02 mmol) in tetrahydrofuran (210 mL) cooled to 0° C. was added triphenylphosphine (5.79 g, 22.07 mmol) followed by diethylazodicarboxylate (3.84 g, 22.07 mmol) and the reaction mixture was allowed to stir at room temperature overnight. The reaction mixture was quenched by the addition of water (10 mL) and the solvent was removed in vacuo to give a crude solid. Purification by flash column chromatography (silica, ethyl acetate:hexanes 1:7) provided 2.93 g (46%) of (±)-tert-butyl(dimethyl)(3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-ylmethoxy)silane as a colorless oil. Rf=0.86 (silica, ethyl acetate:hexanes 1:5); Anal. calcd. for C18H28O2Si: C, 71.0; H, 9.27. Found: C, 69.77; H, 9.21.

Quelle