Benzyl Bromide → 7-Benzyloxy-3-(4-chlorophenyl)-2-isopropyl-4-oxo-4H-chromene-8-carbaldehyde

HRID 14463Notes

Reaction equation

HRID 14463 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17](=[O:18])[C:16]3[C:11](=[C:12]([CH:20]=[O:21])[C:13]([OH:19])=[CH:14][CH:15]=3)[O:10][C:9]=2[CH:22]([CH3:24])[CH3:23])=[CH:4][CH:3]=1.[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[CH2:25]([O:19][C:13]1[C:12]([CH:20]=[O:21])=[C:11]2[C:16]([C:17](=[O:18])[C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)=[C:9]([CH:22]([CH3:24])[CH3:23])[O:10]2)=[CH:15][CH:14]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 866256083-(4-chlorophenyl)-7-hydroxy-2-isopropyl-4-oxo-4H-chromene-8-carbaldehyde

Product 1

HCID 115103077-Benzyloxy-3-(4-chlorophenyl)-2-isopropyl-4-oxo-4H-chromene-8-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(4-chlorophenyl)-7-hydroxy-2-isopropyl-4-oxo-4H-chromene-8-carbaldehyde (7.95 g, 23.2 mmol) and benzyl bromide (7.93 g, 46.4 mmol) in N,N-dimethylformamide (200 ml) is added K2CO3 (9.61 g, 69.5 mmol), and the reaction mixture is stirred at room temperature for 96 h. The mixture is poured into ice/water, extracted with CH2Cl2, dried (MgSO4) and concentrated in vacuo. The resulting solid residue is stirred with hexane/ethyl acetate for 1 h, the solvent is decanted, and the solid is stirred with hexane/diethyl ether for 16 h. The title compound is collected by filtration and washed with hexane to afford a pale brown solid.

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. stirringThe resulting solid residue is stirred with hexane/ethyl acetate for 1 h
  5. customthe solvent is decanted
  6. stirringthe solid is stirred with hexane/diethyl ether for 16 h
  7. filtrationThe title compound is collected by filtration
  8. washwashed with hexane
  9. customto afford a pale brown solid

Sources & evidence

ORD record
ord-7bde9c9bba4e4621a41a66b8d2eaf9a1
Source dataset
uspto-grants-2010_06
Patent number
US07732435B2

Reaction notes

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