Boron trifluoride etherate → HCID 20499032, compound

HRID 2166779Notes

Reaction equation

HRID 2166779 reaction equation
[CH:1]1([CH2:7][NH:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=[O:17])=[CH:11][CH:10]=2)[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1.[CH2:19]([O:21][CH2:22][CH2:23]O)[CH3:20].B(F)(F)F.CCOCC>C1(C)C=CC=CC=1>[CH:1]1([CH2:7][NH:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]([O:18][CH2:20][CH2:19][O:21][CH2:22][CH3:23])=[O:17])=[CH:11][CH:10]=2)[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherate2×HCID 8076Glycol monoethyl etherHCID 20499000HCID 20499000, compound

Product 1

HCID 20499032HCID 20499032, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 11.8 g. of 4-(cyclohex-2-enylmethylamino)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-(cyclohex-2-enylmethylamino)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-64bf5defa700498391ffb7f9cedc5c13
Source dataset
uspto-grants-1983_06
Patent number
US04388459

Reaction notes

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