反応 #1483059

反応方程式

2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9-hexadecafluorodecane-1,10-diol

potassium hydroxide

benzyl bromide

→

10-(benzyloxy)-2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9-hexadecafluorodecan-1-ol

溶媒

DMF

反応条件

後処理

1. 1
   workup.ADDITIONwas added dropwise over 15 minutes
2. 2
   濃縮The reaction mixture was concentrated in vacuo
3. 3
   その他the residue was partitioned between aqueous saturated ammonium chloride and ethyl acetate
4. 4
   抽出The aqueous layer was extracted twice with EtOAc
5. 5
   洗浄washed with water
6. 6
   乾燥brine, dried over MgSO4
7. 7
   濃縮concentrated in vacuo
8. 8
   その他The residue was purified via flash column chromatography on silica gel using 5% EtOAc in petroleum ether as the eluent
9. 9
   その他The product was isolated as colorless oil
10. 10
    その他upon drying under high vacuum for 12 h

実験手順

A dry 5 mL round bottom flask was charged with 2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9-hexadecafluorodecane-1,10-diol (2.2 mmol, 1.0 g), dry DMF (2.5 mL), and crushed potassium hydroxide (2.2 mmol, 121 mg). The mixture was flushed with argon and benzyl bromide (0.7 mmol, 123 mg) was added dropwise over 15 minutes. The solution was allowed to stir overnight at room temperature under argon. The reaction mixture was concentrated in vacuo, and the residue was partitioned between aqueous saturated ammonium chloride and ethyl acetate. The aqueous layer was extracted twice with EtOAc. The organic layers were combined, washed with water then brine, dried over MgSO4, and concentrated in vacuo. The residue was purified via flash column chromatography on silica gel using 5% EtOAc in petroleum ether as the eluent. The product was isolated as colorless oil; upon drying under high vacuum for 12 h, the oil solidified (90%). 1H NMR (CDCl3): δ7.36 (m, 5H), 4.68 (s, 2H), 4.10 (td, 2H, J=14, 6), 3.94 (t, 2H, J=14), 1.96 (t, 1H, J=7); 13C NMR (CDCl3): δ136.6, 128.8, 128.5, 128.0, 74.7, 66.9, 60.9; 19F NMR (CDCl3): δ −119.8, −122.3, −122.8, −123.7, −123.9.

出典