Tetrahydrofuran → HCID 19745866, compound

HRID 2253743Notes

Reaction equation

HRID 2253743 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)=[CH:15][CH:14]=1.[C:21]1(CCC[Mg]Br)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[CH2:32]1C[O:35][CH2:34][CH2:33]1>>[C:21]1([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)[CH2:32][CH2:33][CH2:34][OH:35])[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 145789604-(2-quinolinylmethoxy)BenzaldehydeHCID 178418471HCID 178418471, compound

Product 1

HCID 19745866HCID 19745866, compound

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 (x2), the organic phase was washed with brine (x2), 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 (x2)
  3. washthe organic phase was washed with brine (x2)
  4. customdried
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-a3ec4399072e483789862a0c971e4c33
Source dataset
uspto-grants-1993_08
Patent number
US05232916

Reaction notes

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