Reaction #1483059

Reaction equation

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

Solvents

DMF

Conditions

Workup

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

Procedure

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.

Source