Boron trifluoride etherate → 2-Ethoxyethyl 4-(allylamino)phenylacetate

HRID 1278309Notes

Reaction equation

HRID 1278309 reaction equation
[CH2:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([OH:14])=[O:13])=[CH:7][CH:6]=1)[CH:2]=[CH2:3].[CH2:15]([O:17][CH2:18][CH2:19]O)[CH3:16].B(F)(F)F.CCOCC>C1(C)C=CC=CC=1>[CH2:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([O:14][CH2:16][CH2:15][O:17][CH2:18][CH3:19])=[O:13])=[CH:7][CH:6]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherate2×HCID 8076Glycol monoethyl etherHCID 38316Acetic acid, 2-(p-(allylamino)phenyl)-

Product 1

HCID 211634972-Ethoxyethyl 4-(allylamino)phenylacetate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 11.8 g. of 4-(allylamino)phenylacetic acid, 1.00 g. of 2-ethoxyethanol and 5.35 ml. of boron trifluoride etherate in 200 ml. toluene is stirred under reflux for 48 hours. The solution is treated with an additional 5.35 ml. of boron trifluoride etherate and refluxing is continued for 120 hours. Dilution with water and methylene chloride followed by filtration affords 2-ethoxyethyl 4-(allylamino)phenylacetate.

Workup

  1. temperatureunder reflux for 48 hours
  2. additionThe solution is treated with an additional 5.35 ml
  3. filtrationDilution with water and methylene chloride followed by filtration

Sources & evidence

ORD record
ord-d66ae47ab2a84e54a67f157623781452
Source dataset
uspto-grants-1981_07
Patent number
US04281019

Reaction notes

Loading…