Methyl anisate → 2-(4-Bromopyridin-2-yl)-1-(4-methoxyphenyl)ethanone

HRID 705374

Reaktionsgleichung

Reaktionsgleichung von HRID 705374
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9]C)=O)=[CH:5][CH:4]=1.[Br:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16]([CH3:20])[CH:15]=1.C[Si](C)(C)[N-][Si](C)(C)C.[Li+]>O1CCCC1>[Br:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16]([CH2:20][C:7]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:12][CH:11]=2)=[O:9])[CH:15]=1

Komponenten

5

Edukt 3

HCID 8499Methyl anisateHCID 2733832Lithium HexamethyldisilazideHCID 27628354-Bromo-2-methylpyridine

Produkt 1

HCID 682760292-(4-Bromopyridin-2-yl)-1-(4-methoxyphenyl)ethanoneAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

In a 250 mL round-bottomed flask at 0° C. under nitrogen was added methyl 4-methoxybenzoate (Aldrich, 3.32 g, 20.00 mmol) and 4-bromo-2-methylpyridine (Frontier, 1.72 g, 10.00 mmol) in anhydrous tetrahydrofuran (40.0 mL) to give a yellow solution. Lithium hexamethyldisilazide (1 M in tetrahydrofuran, 20 mL, 20 mmol) was added dropwise over 15 minutes via a dropping addition funnel to produce an orange transparent solution that was stirred for 18 hours at ambient temperature. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried (Na2SO4), filtered and concentrated to a reddish oil. Purification by flash chromatography on a silica 80 g cartridge eluting with 10-60% ethyl acetate in hexane gave the title compound (2.68 g, 88%). MS (APCI+) m/z 306/308 (M+H)+.

Aufarbeitung

  1. customto give a yellow solution
  2. customto produce an orange transparent solution
  3. customThe mixture was partitioned between ethyl acetate and water
  4. washThe organic layer was washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated to a reddish oil
  8. customPurification by flash chromatography on a silica 80 g cartridge
  9. washeluting with 10-60% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-ca36262ee1744184be594846055512b7
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09173887B2

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