p-Anisoyl chloride → LY88074 Trimethyl ether

HRID 1274270Notes

Reaction equation

HRID 1274270 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]3[CH:14]=[C:15]([O:18][CH3:19])[CH:16]=[CH:17][C:11]=3[CH:10]=2)=[CH:5][CH:4]=1.[CH3:20][O:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1.[Cl-].[Al+3].[Cl-].[Cl-].[OH-].[Na+]>ClCCCl.CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]3[CH:14]=[C:15]([O:18][CH3:19])[CH:16]=[CH:17][C:11]=3[C:10]=2[C:26](=[O:27])[C:25]2[CH:29]=[CH:30][C:22]([O:21][CH3:20])=[CH:23][CH:24]=2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 7477p-Anisoyl chlorideHCID 14798Sodium HydroxideHCID 8509416-Methoxy-2-(4-methoxyphenyl)benzo[b]thiopheneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 9953060LY88074 Trimethyl ether

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

2-(4-Methoxyphenyl-6-methoxybenzo[b]thiophene (10 g, (37 mmol) of was dissolved in 700 mL of 1,2-dichloroethane and the mixture cooled to 0° C. To the reaction solution was added, slowly, a mixture of 4-methoxybenzoyl chloride (6.31 g, 37 m mol) and aluminum chloride (5.07 g 38 mmol). The reaction was allowed to proceed at 0° C. for two hours and was terminated by pouring into ice-water. The organic layer was separated and aqueous layer extracted with chloroform. The organic layers were combined, washed with saturated aqueous sodium bicarbonate and water, dried over magnesium sulfate, and filtered. The volatiles were removed by evaporation yielding a yellow oil, which was dissolved in 500 mL of methanol and 15 mL of 5N sodium hydroxide and refluxed until the methanol had evaporated (thirty minutes). The resulting oil was dissolved in diethylether, washed with brine, and evaporated. This yielded 14.6 g of a yellow oil which was purified by chromatography. This yielded 13.9 g of the title compound as a yellow oil. EA calculated for C24H20O4S: C, 71.25; H, 4.98; O, 15.82; S, 7.93. Found: C, 71.25; H, 4.90; O, 15.78; S, 7.65. MS(EI): m/e=404 (M+).

Workup

  1. additionTo the reaction solution was added
  2. customwas terminated
  3. additionby pouring into ice-water
  4. customThe organic layer was separated
  5. extractionaqueous layer extracted with chloroform
  6. washwashed with saturated aqueous sodium bicarbonate and water
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customThe volatiles were removed by evaporation
  10. customyielding a yellow oil, which
  11. customhad evaporated (thirty minutes)
  12. dissolutionThe resulting oil was dissolved in diethylether
  13. washwashed with brine
  14. customevaporated
  15. customThis yielded 14.6 g of a yellow oil which was purified by chromatography

Sources & evidence

ORD record
ord-655f4caaedce4efa86d2029c2c2970d6
Source dataset
uspto-grants-2000_12
Patent number
US06156786

Reaction notes

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