Reaktion #157911

Reaktionsgleichung

DIC

4-(1-phenylcyclohexyl)phenol

BocValOH

→

tert-Butyl 1-((4-(1-phenylcyclohexyl)phenoxy)carbonyl)-2-methylpropylcarbamate

Lösungsmittel

THF

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeprecipitation after a few minutes
2. 2
   EinengenThe reaction mixture was concentrated in vacuo
3. 3
   Sonstigepurified by flash chromatography (eluent: EtOAc (0-10%) in heptane)
4. 4
   Sonstigeaffording 517 mg (1.14 mmol; 93%) of colourless oil

Vorschrift

To a stirred solution at room temperature of 4-(1-phenylcyclohexyl)phenol (311 mg, 1.23 mmol) in dry THF (2 mL) was added BocValOH (295 mg, 1.36 mmol) dissolved in THF (2 mL). A solution of DIC (231 μL; 1.48 mmol) in THF (2 mL) was added drop wise, which caused precipitation after a few minutes. After 5 min DMAP (166 mg; 1.36 mmol) was added and stirring was continued for 19 h. The reaction mixture was concentrated in vacuo and purified by flash chromatography (eluent: EtOAc (0-10%) in heptane) affording 517 mg (1.14 mmol; 93%) of colourless oil. LC-MS purity (UV/MS): 100/100%, Rt 6.77 min, M+18: 469.53.

Quelle