Tetrahydrofuran toluene → 1-(3-(2-(7-Chloro-2-quinolinyl)ethenyl)phenyl)-2-propen-1-ol

HRID 249039Notes

Reaction equation

HRID 249039 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]=[CH:13][C:14]3[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=3)[CH:17]=[O:18])=[N:9]2)=[CH:4][CH:3]=1.[CH:22]([Mg]Br)=[CH2:23].C1(C)C=CC=CC=1.C1COCC1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]=[CH:13][C:14]3[CH:15]=[C:16]([CH:17]([OH:18])[CH:22]=[CH2:23])[CH:19]=[CH:20][CH:21]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 22635083Tetrahydrofuran tolueneHCID 533948533-(2-(7-Chloroquinolin-2-yl)vinyl)benzaldehydeHCID 178418507HCID 178418507, compound

Product 1

HCID 534062851-(3-(2-(7-Chloro-2-quinolinyl)ethenyl)phenyl)-2-propen-1-ol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

To a degassed suspension of 3-(2-(7-chloro-2-quinolinyl)ethenyl)benzaldehyde (U.S. Pat. No. 4,851,409, Example 24, Step 1) (100 g, 0.34 mol) in toluene (700 mL) at 0° C. was slowly added 1.0M vinylmagnesium bromide in toluene/THF (370 mL, 0.37 mol). After stirring for 1 hour at 0° C., the reaction was quenched by the slow addition of saturated NH4Cl solution (150 ml), followed by H2O (500 mL) and HOAc (50 mL). The product was extracted with EtOAc and the two-phase system was filtered through celite to remove an insoluble precipitate. The aqueous phase was then re-extracted with EtOAc (100 mL) and the combined organic layer was washed with H2O, followed by brine. The solution was dried (MgSO4), and evaporated to give a dark yellow residue which was purified by flash chromatography (EtOAc:hexane 1:5, then 1:3). The product was filtered from the column fractions to give a beige solid (67.6 g, mp=110°-112° C.). The filtrate was concentrated and the resulting residue was recrystallized from EtOAc/hexane 1:4 to give a second crop of 15.1 g.

Workup

  1. customat 0° C.
  2. customthe reaction was quenched by the slow addition of saturated NH4Cl solution (150 ml)
  3. extractionThe product was extracted with EtOAc
  4. filtrationthe two-phase system was filtered through celite
  5. customto remove an insoluble precipitate
  6. extractionThe aqueous phase was then re-extracted with EtOAc (100 mL)
  7. washthe combined organic layer was washed with H2O
  8. dry with materialThe solution was dried (MgSO4)
  9. customevaporated
  10. customto give a dark yellow residue which
  11. customwas purified by flash chromatography (EtOAc:hexane 1:5
  12. filtrationThe product was filtered from the column fractions

Sources & evidence

ORD record
ord-099e0db495fc4e4e9fb842baf171d7bf
Source dataset
uspto-grants-1993_05
Patent number
US05212180

Reaction notes

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