반응 #1483059

반응 방정식

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

용매

DMF

반응 조건

후처리

1. 1
   workup.ADDITIONwas added dropwise over 15 minutes
2. 2
   농축The reaction mixture was concentrated in vacuo
3. 3
   기타the residue was partitioned between aqueous saturated ammonium chloride and ethyl acetate
4. 4
   추출The aqueous layer was extracted twice with EtOAc
5. 5
   세척washed with water
6. 6
   건조brine, dried over MgSO4
7. 7
   농축concentrated in vacuo
8. 8
   기타The residue was purified via flash column chromatography on silica gel using 5% EtOAc in petroleum ether as the eluent
9. 9
   기타The product was isolated as colorless oil
10. 10
    기타upon drying under high vacuum for 12 h

실험 절차

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.

출처