4-(2-quinolinylmethoxy)Benzaldehyde → 4-Phenyl-1-(4-(2-quinolinylmethoxy)phenyl)butanol

HRID 1029442Notes

Reaction equation

HRID 1029442 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:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=1.[C:21]1([CH2:27][CH2:28][CH2:29][Mg]Br)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1COCC1>[C:21]1([CH2:27][CH2:28][CH2:29][CH:17]([C:16]2[CH:19]=[CH:20][C:13]([O:12][CH2:11][C:2]3[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[N:1]=3)=[CH:14][CH:15]=2)[OH:18])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 145789604-(2-quinolinylmethoxy)BenzaldehydeHCID 178418471HCID 178418471, compound

Product 1

HCID 100685444-Phenyl-1-(4-(2-quinolinylmethoxy)phenyl)butanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the aldehyde from Step I, (1.34 g) in THF at 0° was added dropwise the 3-phenylpropylmagnesium bromide (1.1 mol. equiv., from above). After 30 mins, the reaction was quenched by the addition of 25% aqueous NH4OAc solution. The mixture was then extracted with ethyl acetate (×2), the organic phase was washed with brine (×2), dried and evaporated under reduced pressure. The title compound was obtained after recrystallization from ethyl acetate/hexane, m.p. 118°-119°.

Workup

  1. customthe reaction was quenched by the addition of 25% aqueous NH4OAc solution
  2. extractionThe mixture was then extracted with ethyl acetate (×2)
  3. washthe organic phase was washed with brine (×2)
  4. customdried
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-f8e9c0338efd461ca9656e4de428a8dd
Source dataset
uspto-grants-1992_04
Patent number
US05102881

Reaction notes

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