Methyl 4-Formylbenzoate → HCID 22282573, compound

HRID 2085351Notes

Reaction equation

HRID 2085351 reaction equation
[Li]CCCC.Br[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=[C:9]([C:17]([CH3:19])=[CH2:18])[CH:8]=1.[CH:20]([C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=1)=[O:21]>C1COCC1>[OH:21][CH:20]([C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=[C:9]([C:17]([CH3:19])=[CH2:18])[CH:8]=1)[C:22]1[CH:23]=[CH:24][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 15294Methyl 4-FormylbenzoateHCID 22282590HCID 22282590, compoundHCID 178418339Butyllithium

Product 1

HCID 22282573HCID 22282573, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of n-BuLi (2.5 M, 7.5 mmol, 3 mL) was added to a solution of (56b) (1.55 g, 6.25 mmol) in 20 mL of anhydrous THF at −78° C. The resulting solution was cannulated to another flask charged with methyl 4-formylbenzoate (1.34 g, 8.1 mmol) in 20 mL of anhydrous THF at −78° C. The reaction mixture was stirred for 3 h at −78° C. before quenched with MeOH. The solution was then diluted with ethyl acetate and washed with H2O and brine, and dried over MgSO4. After filtration and concentration, the residue was purified on silica gel column to provide methyl 4-[hydroxy(2-isopropenyl-4-quinolinyl)methyl]benzoate (0.95 g, 46%). MS (AP+): 333 (M+1).

Workup

  1. customThe resulting solution was cannulated to another flask
  2. custombefore quenched with MeOH
  3. additionThe solution was then diluted with ethyl acetate
  4. washwashed with H2O and brine
  5. dry with materialdried over MgSO4
  6. filtrationAfter filtration and concentration
  7. customthe residue was purified on silica gel column

Sources & evidence

ORD record
ord-6ade83724ba84693bc0503054e54e560
Source dataset
uspto-grants-2004_04
Patent number
US06720329B2

Reaction notes

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