Sodium Methoxide → HCID 15840672, compound

HRID 342760Notes

Reaction equation

HRID 342760 reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][C:12](=O)N(C)C)=[C:7]([Cl:17])[CH:6]=1.C[O-].[Na+].BrC[CH2:24][CH2:25][O:26][C:27]1[C:36]([CH2:37][CH2:38][CH3:39])=[C:35]2[C:30]([CH:31]=[C:32]([CH2:41][CH3:42])[C:33](=[O:40])[O:34]2)=[CH:29][CH:28]=1>CO>[Cl:17][C:7]1[CH:6]=[C:5]([CH2:4][C:3]([O:2][CH3:1])=[O:18])[CH:10]=[CH:9][C:8]=1[S:11][CH2:12][CH2:24][CH2:25][O:26][C:27]1[C:36]([CH2:37][CH2:38][CH3:39])=[C:35]2[C:30]([CH:31]=[C:32]([CH2:41][CH3:42])[C:33](=[O:40])[O:34]2)=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 15840683HCID 15840683, compoundHCID 53811470HCID 53811470, compound

Product 1

HCID 15840672HCID 15840672, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Conditions

Temperature
70 °C

Procedure

To a solution of 3-chloro-4-dimethylcarbamoylthiophenylacetic acid methyl ester (54 mg, 0.1656 mmol) in 0.50 mL methanol was added a 0.5M solution of sodium methoxide (0.33 mL, 0.1656 mmol) in methanol. This mixture was heated to 70° C. for 90 minutes. After cooling to ambient temperature, a solution of 7-(3-bromopropoxy)-3-ethyl-8-propylcoumarin (Step D; 54 mg, 0.1656 mmol) in 1.2 mL methanol was added dropwise. The mixture was heated to 70° C. for several hours. The reaction mixture was concentrated in vacuo and diluted with ethyl acetate. The organic mixture was washed with water, brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude residue was purified by flash chromatography on silica gel (20% ethyl acetate/hexane) to provide the title compound.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. temperatureThe mixture was heated to 70° C. for several hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. additiondiluted with ethyl acetate
  5. washThe organic mixture was washed with water, brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude residue was purified by flash chromatography on silica gel (20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-2a074b0605894aec87590c4ad9e8eae8
Source dataset
uspto-grants-1999_01
Patent number
US05859051

Reaction notes

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