Boron trifluoride etherate → HCID 20499032, compound

HRID 128333Notes

Reaction equation

HRID 128333 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-9a017403e4ca461da575d3f4237c1dac
Source dataset
uspto-grants-1981_03
Patent number
US04259352

Reaction notes

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