Triethylamine → HCID 19022261, compound

HRID 1109285Notes

Reaction equation

HRID 1109285 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]([C:9]1[O:10][CH:11]=[CH:12][CH:13]=1)([OH:8])[C:4]([F:7])([F:6])[F:5].C(N(CC)CC)C.[F:23][C:24](=[CH2:28])[C:25](Cl)=[O:26]>C(OCC)C>[F:23][C:24](=[CH2:28])[C:25]([O:8][C:3]([C:9]1[O:10][CH:11]=[CH:12][CH:13]=1)([C:2]([F:1])([F:14])[F:15])[C:4]([F:7])([F:6])[F:5])=[O:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 565743HCID 565743, compoundHCID 27833352-Fluoroacryloyl chloride

Product 1

HCID 19022261HCID 19022261, compoundYield 61.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
20 °C

Procedure

A solution of 20 g (0.085 mol) of hexafluoro-2-(2-furyl)-2-propanol and 8.65 g (0.085 mol) of triethylamine in 25 ml of dry diethyl ether was added dropwise with stirring at a temperature of 20° C. to a solution of 9.8 g (0.09 mol) of α-fluoroacryloyl chloride (obtained according to Example 4) in 25 ml of dry diethyl ether in the course of 30 minutes. The reaction mixture was then stirred at a temperature of 20° C. for a further 4 hours. The resulting solid was filtered off. The filtrate was distilled under reduced pressure after addition of 0.005 g of hydroquinone monomethyl ether. 15.9 g (61 percent of theory) of hexafluoro-2-(2-furyl)-2-propyl α-fluoroacrylate having a boiling point of 55° to 57° C. (under 8 mbar) were obtained.

Workup

  1. filtrationThe resulting solid was filtered off
  2. distillationThe filtrate was distilled under reduced pressure
  3. additionafter addition of 0.005 g of hydroquinone monomethyl ether

Sources & evidence

ORD record
ord-b1627498f5f947e692960f55b18db37f
Source dataset
uspto-grants-1994_06
Patent number
US05319131

Reaction notes

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