Réaction #76388

Équation de réaction

( 3 )

2-Benzyloxy-6-bromo-naphthalene

4-(5,5,6,6,7,7,8,8,8-nonafluoro-octyl)-tosylate

4-(5,5,6,6,7,7,8,8,8-nonafluoro-octyloxy)-tosylate

→

2-(5,5,6,6,7,7,8,8,8-nona fluoro-octyl)-buta-1,3-diene

2-(5,5,6,6,7,7,8,8,8-Nonafluoro-octyl)-buta-1,3-diene

Solvants

THF

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas added at ice temperature over a period of 20 min
2. 2
   Autrequenched with 5% aqueous ammonium chloride (1 mL/mmole)
3. 3
   Extractionextracted with hexane
4. 4
   Lavagewashed with brine
5. 5
   Séchagedried over MgSO4
6. 6
   Concentrationconcentrated in vacuo
7. 7
   AutrePurification by chromatography on silica gel (hexane)

Mode opératoire

To a solution of 4-(5,5,6,6,7,7,8,8,8-nonafluoro-octyl)-tosylate (10), (1 equi) and copper (I) bromide (0.05 equi.) in THF (2 mL/mmole), a solution of buta-1,3-diene-2-magnesium chloride, prepared as described in (3), (38) (0.5M in THF) (1.3 equi.) was added at ice temperature over a period of 20 min. The reaction mixture was stirred at room temperature for 24 h, quenched with 5% aqueous ammonium chloride (1 mL/mmole), extracted with hexane, washed with brine, dried over MgSO4, and concentrated in vacuo. Purification by chromatography on silica gel (hexane) gave 2-(5,5,6,6,7,7,8,8,8-nona fluoro-octyl)-buta-1,3-diene (39) a colorless oil (96%).

Source