Reaktion #48767

ord-fa9ad0d0566c4cd08fb041abb5de3527

Reaktionsgleichung

C[C@@H](O)CO[Si](C)(C)C(C)(C)C
(2R)-1-{[tert-Butyl(dimethyl)silyl]oxy}propan-2-ol
COC(=O)c1cc(O)cc(Oc2ccc(S(C)(=O)=O)cc2)c1
methyl 3-hydroxy-5-[4-(methylsulfonyl)phenoxy]benzoate
c1ccc(P(c2ccccc2)c2ccccc2)cc1
triphenylphosphine
CC(C)OC(=O)/N=N/C(=O)OC(C)C
DIAD
→
COC(=O)c1cc(Oc2ccc(S(C)(=O)=O)cc2)cc(O[C@@H](C)CO[Si](C)(C)C(C)(C)C)c1
title compound
Ausbeute 87.3%
COC(=O)c1cc(Oc2ccc(S(C)(=O)=O)cc2)cc(O[C@@H](C)CO[Si](C)(C)C(C)(C)C)c1
Methyl 3-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-5-[4-(methylsulfonyl)phenoxy]benzoate
Ausbeute 87.3%

Edukte

C[C@@H](O)CO[Si](C)(C)C(C)(C)C
(2R)-1-{[tert-Butyl(dimethyl)silyl]oxy}propan-2-ol
COC(=O)c1cc(O)cc(Oc2ccc(S(C)(=O)=O)cc2)c1
methyl 3-hydroxy-5-[4-(methylsulfonyl)phenoxy]benzoate
c1ccc(P(c2ccccc2)c2ccccc2)cc1
triphenylphosphine
CC(C)OC(=O)/N=N/C(=O)OC(C)C
DIAD

Reagenzien

Keine

Lösungsmittel

ClCCl
DCM

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigePurification by column chromatography
  2. 2
    Wascheneluting with 1:4 to 1:2 ethyl acetate

Vorschrift

(2R)-1-{[tert-Butyl(dimethyl)silyl]oxy}propan-2-ol (2.18 g, 11.47 mmol) was added to a solution of methyl 3-hydroxy-5-[4-(methylsulfonyl)phenoxy]benzoate (2.76 g, 8.57 mmol) in dry DCM (100 mL) followed by addition of polymer-supported triphenylphosphine (3.0 mmol/g (Fluka), 8.57 g, 25.71 mmol) and DIAD (3.37 mL, 17.1 mmol) at RT. The reaction was stirred for 3 h before filtration through diatomaceous earth and evaporation. Purification by column chromatography, eluting with 1:4 to 1:2 ethyl acetate:hexanes, afforded the title compound as a colourless oil (3.70 g, 87%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07745475B2uspto-grants-2010_06