Diethyl Ether → HCID 22490868, compound

HRID 2180556Notes

Reaction equation

HRID 2180556 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:14])([CH3:13])[CH2:7][CH2:8][C:9]2=O)=[CH:4][C:3]=1[O:15][CH2:16][CH3:17].N1C=CC=N[C:19]1=O.C[Mg]Br.C(OCC)C>C1COCC1>[Br:1][C:2]1[CH:11]=[C:10]2[C:5](=[CH:4][C:3]=1[O:15][CH2:16][CH3:17])[C:6]([CH3:14])([CH3:13])[CH2:7][CH:8]=[C:9]2[CH3:19]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 684012(1H)-PyrimidinoneHCID 22490916HCID 22490916, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 22490868HCID 22490868, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 7-bromo-6-ethoxy-4,4-dimethyl-3,4-dihydro-2H-naphthalen-1-one (Compound A-4, 1.05 g, 3.53 mmol) in THF (12 mL) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1])-pyrimidinone (2 mL) at 0° C. was added a solution of methylmagnesium bromide (3M in diethylether (3.53 mL, 10.59 mmol). The reaction was allowed to warm up to room temperature and was stirred at 50° C. overnight. The reaction was quenched with ice water and extracted with diethylether. The organic layer was washed successively with water, brine, dried over Na2SO4, and concentrated in vacuo. The crude material was then dissolved in benzene (20 mL). After catalytic amount of p-toluenesulfonic acid was added, the reaction was stirred at reflux for 2 h. The solvent was removed in vacuo. The residue was purified by column chromatography (silica gel, 1% ethyl acetate in hexane) to afford the title compound as a pale yellow oil.

Workup

  1. customThe reaction was quenched with ice water
  2. extractionextracted with diethylether
  3. washThe organic layer was washed successively with water, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. dissolutionThe crude material was then dissolved in benzene (20 mL)
  7. additionAfter catalytic amount of p-toluenesulfonic acid was added
  8. stirringthe reaction was stirred
  9. temperatureat reflux for 2 h
  10. customThe solvent was removed in vacuo
  11. customThe residue was purified by column chromatography (silica gel, 1% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-9dfde64129d249c59346748ab40a9b48
Source dataset
uspto-grants-2005_05
Patent number
US06887896B1

Reaction notes

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