Water → HCID 23114108, compound

HRID 1787325Notes

Reaction equation

HRID 1787325 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[C:13]3[C:14]([CH3:28])=[C:15]([NH:20][C:21](=[O:27])[CH2:22][C:23]([CH3:26])([CH3:25])[CH3:24])[C:16]([CH3:19])=[C:17]([CH3:18])[C:12]=3[O:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1.[Cl-].[Al+3].[Cl-].[Cl-].[C:33](Cl)(=[O:35])[CH3:34].O>ClCCl>[C:33]([C:8]1[CH:7]=[CH:6][C:5]([CH:9]2[C:13]3[C:14]([CH3:28])=[C:15]([NH:20][C:21](=[O:27])[CH2:22][C:23]([CH3:24])([CH3:25])[CH3:26])[C:16]([CH3:19])=[C:17]([CH3:18])[C:12]=3[O:11][CH2:10]2)=[CH:4][C:3]=1[O:2][CH3:1])(=[O:35])[CH3:34]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 23114138HCID 23114138, compound

Product 1

HCID 23114108HCID 23114108, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(3-(3-methoxyphenyl)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide (1.0 g, 2.62 mmol) obtained in Example 72 in dichloromethane (20 mL) was added at −50° C. under an argon atmosphere aluminum chloride (769 mg, 5.77 mmol) and the resulting mixture was stirred for 10 minutes. To the reaction solution was added dropwise at the same temperature acetyl chloride (0.62 mL, 8.65 mmol and the resulting mixture was warmed to room temperature. The reaction solution was added to water and the product was extracted with ethyl acetate. The combined organic layers were washed with an aqueous saturated sodium hydrogen carbonate solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 993 mg (yield: 89%) of the title compound. Melting point: 131-133° C. (ethyl acetate-hexane).

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe combined organic layers were washed with an aqueous saturated sodium hydrogen carbonate solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-34246ebfd074467796614738a5990535
Source dataset
uspto-grants-2009_03
Patent number
US07507841B2

Reaction notes

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