p-Anisoyl chloride → LY88074 Trimethyl ether

HRID 377419Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 377419
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:15][C:14]3[CH:16]=[C:17]([O:20][CH3:21])[CH:18]=[CH:19][C:13]=3[CH:12]=2)=[CH:7][CH:6]=1.[C:22](Cl)(=[O:31])[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1.B(Cl)(Cl)Cl>CO.C(Cl)Cl>[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:15][C:14]3[CH:16]=[C:17]([O:20][CH3:21])[CH:18]=[CH:19][C:13]=3[C:12]=2[C:22](=[O:31])[C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)=[CH:7][CH:6]=1

Komponenten

7

Edukt 4

HCID 7477p-Anisoyl chlorideHCID 14798Sodium HydroxideHCID 25135Boron TrichlorideHCID 8509416-Methoxy-2-(4-methoxyphenyl)benzo[b]thiophene

Produkt 1

HCID 9953060LY88074 Trimethyl etherAusbeute 89,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A 250 mL, 3 neck, round bottomed flask fitted with a mechanical agitator and connected to a sodium hydroxide scrubber is purged with nitrogen and charged with 2-(4-methoxyphenyl)-6-methoxybenzo[b]thiophene (5.3 g, 19.6 mmol), p-anisoyl chloride (3.68 g, 21.56 mmol), and 100 mL of methylene chloride. To this slurry at 20° C. is added boron trichloride (3.4 mL, 39.8 mmol) which had been condensed in a graduated cylinder. The reaction mixture is quenched after 40 minutes by the slow addition of 50 mL of methanol over approximately 5 minutes followed by addition of 50 mL of water over 5 minutes. The organic phase is washed with 50 mL brine, dried over sodium sulfate, filtered, and concentrated affording a dark orange oil. Addition of 10 mL of methanol followed by sonication for 5 minutes resulted in crystallization of 7.1 g of crude product as a yellow solid. The crude material is recrystallized from 3:1 hexanes/toluene affording 5.9 g of product as pale yellow crystals. (75%).

Aufarbeitung

  1. customA 250 mL, 3 neck, round bottomed flask fitted with a mechanical agitator
  2. customis purged with nitrogen
  3. customcondensed in a graduated cylinder
  4. customThe reaction mixture is quenched after 40 minutes by the slow addition of 50 mL of methanol over approximately 5 minutes
  5. additionfollowed by addition of 50 mL of water over 5 minutes
  6. washThe organic phase is washed with 50 mL brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customaffording a dark orange oil
  11. customfollowed by sonication for 5 minutes

Quellen und Nachweise

ORD-Eintrag
ord-99d01f4435d74c2eb3158d6a7e6cd304
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06025495

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