Hydrochloric Acid → 2,2-Dimethyl-7-(2-dimethylaminoethoxy)-4-phenyl-2H-chromene

HRID 262139Notes

Reaction equation

HRID 262139 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:9][C:10]1([CH3:27])[CH2:19][C:18](=O)[C:17]2[C:12](=[CH:13][C:14]([O:21][CH2:22][CH2:23][N:24]([CH3:26])[CH3:25])=[CH:15][CH:16]=2)[O:11]1.Cl>C1COCC1.CCOCC>[CH3:9][C:10]1([CH3:27])[CH:19]=[C:18]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:17]2[C:12](=[CH:13][C:14]([O:21][CH2:22][CH2:23][N:24]([CH3:26])[CH3:25])=[CH:15][CH:16]=2)[O:11]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 205705632,2-Dimethyl-7-(2-dimethylaminoethoxy)-4-chromanoneHCID 178418255HCID 178418255, compound

Product 1

HCID 205705072,2-Dimethyl-7-(2-dimethylaminoethoxy)-4-phenyl-2H-chromene

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of phenylmagnesium bromide [from bromobenzene and magnesium in dry tetrahydrofuran] was added 2,2-dimethyl-7-(2-dimethylaminoethoxy)-chroman-4-one in dry THF and the resulting solution was boiled under reflux for 2 weeks. The cooled reaction mixture was decomposed with 2.5 N hydrochloric acid and the organic layer separated and dried (magnesium sulphate). Removal of the solvent gave a yellow oil which was chromatograhed on silica in 3% ether-97% light petroleum (b.p. 60°-80°) gave the title compound as a colourless oil. Dissolution in dry ether and passage of dry hydrogen chloride through the solution gave the hydrochloride salt, m.p. 186.5°-187.5°. An analogous procedure yielded 7-(2-N-benzyl-N-methyl-aminoethoxy)-4-(4-fluorophenyl)-2,2-dimethyl-2H-chromene as a colourless oil.

Workup

  1. temperatureunder reflux for 2 weeks
  2. customThe cooled reaction mixture
  3. customthe organic layer separated
  4. dry with materialdried (magnesium sulphate)
  5. customRemoval of the solvent
  6. customgave a yellow oil which

Sources & evidence

ORD record
ord-9934261da32f43b091179e2b8dad1730
Source dataset
uspto-grants-1979_05
Patent number
US04153617

Reaction notes

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