Reaction #997653

Reaction equation

ethanolamine

Perfluoro-2-methyl-3-oxahexanoyl fluoride

→

N-(perfluoro-2-methyl-3-oxahexanoyl)-2-aminoethanol

Solvents

ether

Conditions

Workup

1. 1
   Otherthe reaction temperature below 25° C
2. 2
   workup.ADDITIONAfter the addition
3. 3
   OtherThe solid was removed by filtration
4. 4
   Washthe filtrate was washed with hydrochloric acid (0.5N, 30 mL), water (2 times 30 mL), sodium hydrogen carbonate solution (0.5N, 20 mL), water (30 mL), and sodium chloride solution (saturated, 20 mL)
5. 5
   ConcentrationIt was then concentrated
6. 6
   Otherdried in vacuum over night at room temperature

Procedure

A mixture of ethanolamine (13 g, 28 mmol) and ether (30 mL) was cooled to 15° C. Perfluoro-2-methyl-3-oxahexanoyl fluoride (33 g in ether 50 mL) was added dropwise to keep the reaction temperature below 25° C. After the addition, the reaction mixture was stirred at room temperature for one hour. The solid was removed by filtration and the filtrate was washed with hydrochloric acid (0.5N, 30 mL), water (2 times 30 mL), sodium hydrogen carbonate solution (0.5N, 20 mL), water (30 mL), and sodium chloride solution (saturated, 20 mL). It was then concentrated and dried in vacuum over night at room temperature to give N-(perfluoro-2-methyl-3-oxahexanoyl)-2-aminoethanol as a white solid 35 g, yield 95%. mp. 69-72° C. 1H NMR (CDCl3) δ 1.67 (bs, 1H), 3.57 (m, 2H), 3.80 (t, J=5 Hz, 2H), 6.91 (bs, 1H).

Source