Diethyl Ether → HCID 10752374, compound

HRID 345856Notes

Reaction equation

HRID 345856 reaction equation
[I-].[C:2]1([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][CH2:10][N+:9]=2[CH3:18])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:19](OCC)C.C[Mg]Br.[Cl-].[NH4+]>O1CCCC1.C(OCC)(=O)C>[CH3:19][C:8]1([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10][N:9]1[CH3:18]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 10521731HCID 10521731, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 10752374HCID 10752374, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 1-phenyl-2-methyl-3,4-dihydroisoquinolinium iodide (1.0 g) in tetrahydrofuran (15 ml) was added 3M diethyl ether solution of methyl magnesium bromide (1.9 ml) with stirring at room temperature. After stirring for 30 minutes, the mixture was poured into saturated ammonium chloride aqueous solution and ethyl acetate. The organic layer was washed with water, sodium chloride aqueous solution and dried over magnesium sulfate, and evaporated in vacuo. The residue was recrystallized from n-hexane to give 1,2-dimethyl-1-phenyl-1,2,3,4-tetrahydroisoquinoline (0.6 g).

Workup

  1. stirringAfter stirring for 30 minutes
  2. washThe organic layer was washed with water, sodium chloride aqueous solution
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was recrystallized from n-hexane

Sources & evidence

ORD record
ord-6c1441b1ac2a4f198b360c0d349df31c
Source dataset
uspto-grants-1991_10
Patent number
US05059608

Reaction notes

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