Reaktion #48785

Reaktionsgleichung

DIAD

(2R)-1-{[tert-Butyl(dimethyl)silyl]oxy}propan-2-ol

methyl 3-hydroxy-5-{[phenylmethyl]oxy}benzoate

triphenylphosphine

→

title compound

Ausbeute 80.1%

Methyl 3-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-5-[(phenylmethyl)oxy]benzoate

Ausbeute 80.1%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction was quenched with water (100 mL) and diethyl ether (400 mL)
2. 2
   Sonstigethe organic layer was separated
3. 3
   Trocknenthen dried (MgSO4)
4. 4
   Sonstigeevaporated
5. 5
   SonstigePurification by column chromatography
6. 6
   Wascheneluting with 1:15 to 1:5 ethyl acetate

Vorschrift

(2R)-1-{[tert-Butyl(dimethyl)silyl]oxy}propan-2-ol (3.31 g, 17.4 mmol) was added to a solution of methyl 3-hydroxy-5-{[phenylmethyl]oxy}benzoate (3.00 g, 11.6 mmol) in THF (50 mL) at 0° C. followed by addition of triphenylphosphine (4.57 g, 17.4 mmol) then DIAD (3.43 mL, 17.4 mmol) and the reaction was warmed to RT and stirred for 16 h. The reaction was quenched with water (100 mL) and diethyl ether (400 mL) and the organic layer was separated then dried (MgSO4) and evaporated. Purification by column chromatography, eluting with 1:15 to 1:5 ethyl acetate:hexane, afforded the title compound as a colourless oil (4.00 g, 80%).

Quelle