HCID 10505429, compound → HCID 10625577, compound

HRID 1957297Notes

Reaction equation

HRID 1957297 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:38]=[CH:37][C:16]([C:17]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]3[CH:36]=[CH:35][C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[N:28]=3)=[CH:21][CH:20]=2)=[O:18])=[CH:15][CH:14]=1.[CH3:39][Mg]Br>C1COCC1>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([C:17]([C:19]2[CH:20]=[CH:21][C:22]([O:25][CH2:26][C:27]3[CH:36]=[CH:35][C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[N:28]=3)=[CH:23][CH:24]=2)([OH:18])[CH3:39])=[CH:37][CH:38]=1

Participants

4

Reactant 2

HCID 10505429HCID 10505429, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 10625577HCID 10625577, compoundYield 89.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4,4'-di(2-quinolylmethoxy)benzophenone (992 mg, 2 mmol) in THF (20 mL) at -78° C. was added methylmagnesium bromide (3M solution in ethyl ether, 0.8 mL, 2.4 mmol) and the resulting mixture was stirred at room temperature for 12 hours. The mixture was then quenched with saturated aqueous NH4Cl and extracted with ethyl acetate. The extract was washed with water, brine, dried with anhydrous MgSO4 and concentrated in vacuo. The residue was chromatographed (silica gel, methylene chloride-ethyl acetate 4:1) to afford 920 mg of 1,1-bis(4-(2-quinolylmethoxy)phenyl)ethanol.

Workup

  1. customThe mixture was then quenched with saturated aqueous NH4Cl
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water, brine
  4. dry with materialdried with anhydrous MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed (silica gel, methylene chloride-ethyl acetate 4:1)

Sources & evidence

ORD record
ord-345cc040a810478b91d7f1bc794729ab
Source dataset
uspto-grants-1998_07
Patent number
US05783586

Reaction notes

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