p-Anisoyl chloride → LY88074 Trimethyl ether

HRID 354084Notes

Reaction equation

HRID 354084 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)[S:8][C:7]=2[CH:19]=1.[C:20](Cl)(=[O:29])[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1.[Cl-].[Cl-].[Cl-].[Al+3]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:20]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)=[O:29])=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=3)[S:8][C:7]=2[CH:19]=1

Participants

5

Reactant 3

HCID 7477p-Anisoyl chlorideHCID 8509416-Methoxy-2-(4-methoxyphenyl)benzo[b]thiopheneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 9953060LY88074 Trimethyl ether

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 6-methoxy-2-(4-methoxyphenyl) -benzo[b]thiophene (2 g, 7.4 mmol), and ρ-anisoyl chloride in 110 mL of methylene chloride was added aluminum trichloride (4.93 g, 37 mmol) in three portions and the reaction was stirred overnight. It was then quenched with 200 mL of 2N sodium hydroxide and extracted with methylene chloride. The combined organic layers was washed with brine and dried over anhydrous magnesium sulfate. After filtration, concentration and silica gel column chromatography using 15% ethyl acetate—hexanes as eluant the title compound (1.73 g) was obtained.

Workup

  1. customIt was then quenched with 200 mL of 2N sodium hydroxide
  2. extractionextracted with methylene chloride
  3. washThe combined organic layers was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter filtration, concentration and silica gel column chromatography
  6. customwas obtained

Sources & evidence

ORD record
ord-b71cccf74d2f4293a8e31d35c2627f28
Source dataset
uspto-grants-2004_06
Patent number
US06756388B1

Reaction notes

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