Ethyl Acetate → HCID 22241476, compound

HRID 892132Notes

Reaction equation

HRID 892132 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:14]=[C:15]([OH:19])[CH:16]=[CH:17][CH:18]=1.Br[CH2:21][C:22]1[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[C:23]=1[C:24]([O:26][CH3:27])=[O:25].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C=O)C>[CH3:21][C:22]1[CH:31]=[CH:30][CH:29]=[C:28]([CH2:32][O:19][C:15]2[CH:16]=[CH:17][CH:18]=[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]=2)[C:23]=1[C:24]([O:26][CH3:27])=[O:25]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 10263795Methyl 2-(bromomethyl)-6-methylbenzoateHCID 10988736Phenol, 3-(2-quinolinylmethoxy)-

Product 1

HCID 22241476HCID 22241476, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

13-(Quinolin-2-ylmethoxy)-phenol (5.2 g, 21 mmol, example 3), methyl 2-bromomethyl-6-methyl-benzoate (example 2) (5.0 g, 21 mmol) and potassium carbonate (4.4 g, 32 mmol) are combined in DMF (50 mL) and heated at 85° C. for 3 h. The reaction is poured into ethyl acetate (500 mL) and washed with water (4×120 mL) and brine (100 mL). The solution is dried over magnesium sulfate, filtered and concentrated in vacuo to provide a residue which is purified by column chromatography (silica, 10 to 20% ethyl acetate in hexane) to provide the title compound. MS (ESI) 414 (M+H)+.

Workup

  1. washwashed with water (4×120 mL) and brine (100 mL)
  2. dry with materialThe solution is dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto provide a residue which
  6. customis purified by column chromatography (silica, 10 to 20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-cf1ccdfa8c5c4910b8291994e1d57646
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Reaction notes

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