Reaktion #601206

Reaktionsgleichung

n-BuLi

(S)-ethyl 2-tert-butoxy-2-(1-(4-chlorophenyl)-3-formylnaphthalen-2-yl)acetate

n-BuLi

→

desired product

(S)-ethyl 2-tert-butoxy-2-(1-(4-chlorophenyl)-3-vinylnaphthalen-2-yl)acetate

Lösungsmittel

THF

THF

EtOAc

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONThis mixture was added to another mixture, which
2. 2
   workup.STIRRINGstirred at −78° C. for 15 min
3. 3
   Temperaturto warm to room temperature
4. 4
   workup.STIRRINGstirred at room temperature for 1 h
5. 5
   Waschenwashed with sat. NH4Cl
6. 6
   Extraktionextracted with EtOAc
7. 7
   Trocknendried over MgSO4
8. 8
   Filtrationfiltered
9. 9
   Einengenconcentrated in vacuo
10. 10
    Sonstigepurified by flash column chromatography (silica gel, ethyl acetate/hexanes)

Vorschrift

To a suspension of methyltriphenylphosphonium bromide (60 mg, 0.168 mmol) in THF (1 mL) at −78° C. was added dropwise n-BuLi (1.6 M in hexanes, 90 μL), followed after 30 min by a solution of (S)-ethyl 2-tert-butoxy-2-(1-(4-chlorophenyl)-3-formylnaphthalen-2-yl)acetate (12 mg, 0.028 mmol) in THF (1 mL). The reaction mixture was allowed to warm to room temperature and stirred at room temperature for 2 hours. This mixture was added to another mixture, which was made by adding n-BuLi (1.6 M in hexanes, 300 μL) to a suspension of methyltriphenylphosphonium bromide (200 mg, 0.56 mmol) in THF (2 mL) and stirred at −78° C. for 15 min. Then the reaction mixture was allowed to warm to room temperature and stirred at room temperature for 1 h. The reaction mixture was diluted with EtOAc, washed with sat. NH4Cl, and extracted with EtOAc. The organic layers were combined, dried over MgSO4, filtered, concentrated in vacuo and purified by flash column chromatography (silica gel, ethyl acetate/hexanes) to provide 7.4 mg of the desired product. 1H-MNR 400 MHz (CDCl3) δ: 7.95 (s, 1H), 7.78 (d, J=4.2 Hz, 1H), 7.57-7.50 (m, 1H), 7.43-7.17 (m, 6H), 5.62 (dd, J=8.1, 2 Hz, 1H), 5.25 (dd, J=5.3, 1.8 Hz, 1H), 5.07 (s, 1H), 4.06-4.02 (m, 2H), 1.10 (t, J=7 Hz, 3H), 0.93 (s, 9H).

Quelle