N,N-Diethylaniline → HCID 66760441, compound

HRID 1850421Notes

Reaction equation

HRID 1850421 reaction equation
C(N(CC)[C:4]1[CH:9]=[CH:8]C=CC=1)C.[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19]CC(C)=C)[C:14]=1[CH3:24].[C:25](OCC)(=O)C>>[Cl:12][C:13]1[C:14]([CH3:24])=[C:15]([OH:19])[C:16]([CH2:25][C:9]([CH3:8])=[CH2:4])=[CH:17][CH:18]=1

Participants

4

Reactant 3

HCID 7061N,N-DiethylanilineHCID 8857Ethyl AcetateHCID 66760065HCID 66760065, compound

Product 1

HCID 66760441HCID 66760441, compoundYield 96%

Procedure

A solution of N,N-diethylaniline (12.1 mL) containing 1-chloro-2-methyl-3-[(2-methylprop-2-en-1-yl)oxy]benzene (3.00 mg, 15.3 mmol) synthesized in Reference Example 153 was reacted under microwave irradiation at 220° C. for 20 minutes. After cooled to room temperature, the reaction solution was diluted with ethyl acetate, and washed serially with 1N hydrochloric acid, saturated sodium bicarbonate water and saturated saline. It was dried using anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. After that, the obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate 10:1) to give 2.89 g of the title compound as a yellow solid (yield: 96%).

Workup

  1. customsynthesized in Reference Example 153
  2. customwas reacted under microwave irradiation at 220° C. for 20 minutes
  3. washwashed serially with 1N hydrochloric acid, saturated sodium bicarbonate water and saturated saline
  4. customIt was dried
  5. customthe solvent was removed under reduced pressure
  6. customAfter that, the obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate 10:1)

Sources & evidence

ORD record
ord-7703ee38a65f46fca58680e2b02c637f
Source dataset
uspto-grants-2015_02
Patent number
US08957069B2

Reaction notes

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