Reaktion #1491

ord-54921a0488e14a3e81bfab9c9a8565e8

Reaktionsgleichung

CC1(C)CC=C(c2cccs2)c2cc(C(=O)Oc3ccc(C(=O)OCC[Si](C)(C)C)cc3)ccc21
2-trimethylsilylethyl 4-[[(5,5-dimethyl-5,6-dihydro-8-(2-thienyl)-naphthalen-2-yl)carbonyl]oxy]-benzoate
CCCC[N+](CCCC)(CCCC)CCCC.[F-]
tetrabutylammonium fluoride
CC1(C)CC=C(c2cccs2)c2cc(C(=O)Oc3ccc(C(=O)O)cc3)ccc21
4-[[(5,5-Dimethyl-5,6-dihydro-8-(2-thienyl)-naphthalen-2-yl)carbonyl]oxy]-benzoic acid

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Waschenwashed with H2O and saturated aqueous NaCl
  2. 2
    Trocknenbefore being dried over MgSO4
  3. 3
    SonstigeThe solvents were removed under reduced pressure
  4. 4
    Waschenthe residue washed with hot acetonitrile leaving the product as a colorless solid

Vorschrift

To a solution of 2-trimethylsilylethyl 4-[[(5,5-dimethyl-5,6-dihydro-8-(2-thienyl)-naphthalen-2-yl)carbonyl]oxy]-benzoate (Compound E10, 100.0 mg, 0.198 mmol) in 2.0 mL THF at room temperature was added 155.3 mg of tetrabutylammonium fluoride (0.594 mmol 0.6 mL of a 1M solution in THF). After stirring overnight the reaction was diluted with EtOAc and washed with H2O and saturated aqueous NaCl before being dried over MgSO4. The solvents were removed under reduced pressure and the residue washed with hot acetonitrile leaving the product as a colorless solid.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05723666uspto-grants-1998_03