Triethylamine → 5-Bromo-2-(3,6-dihydro-2H-pyran-4-yl)-3-methylpyridine

HRID 1748563Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1748563
[Br:1][C:2]1[CH:3]=[C:4]([CH3:15])[C:5]([C:8]2(O)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[N:6][CH:7]=1.C(N(CC)CC)C.Cl.CN(C)C.S(Cl)(C)(=O)=O>C1(C)C=CC=CC=1.O>[Br:1][C:2]1[CH:3]=[C:4]([CH3:15])[C:5]([C:8]2[CH2:13][CH2:12][O:11][CH2:10][CH:9]=2)=[N:6][CH:7]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 10313079Trimethylamine HydrochlorideHCID 866925094-(5-Bromo-3-methylpyridin-2-yl)-tetrahydro-2H-pyran-4-ol

Produkt 1

HCID 866925085-Bromo-2-(3,6-dihydro-2H-pyran-4-yl)-3-methylpyridineAusbeute 86,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

4-(5-Bromo-3-methylpyridin-2-yl)-tetrahydro-2H-pyran-4-ol (2.95 g), triethylamine (3 ml) and trimethylamine monohydrochloride (103 mg) were suspended in toluene (50 ml), mesyl chloride (1.26 ml) was added thereto under ice-cooling, then warmed to room temperature, and stirred for 72 hours. After completion of the reaction, water was added thereto, extracted with chloroform, the organic layer was dried over anhydrous sodium sulfate, and then the solvent was evaporated in vacuo. The obtained residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) to give the titled compound (2.39 g) as a white solid. MS (ESI) m/z: 254, 256 (M+H)+.

Aufarbeitung

  1. temperatureunder ice-cooling
  2. additionwas added
  3. extractionextracted with chloroform
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated in vacuo
  6. customThe obtained residue was purified with silica gel column chromatography (n-hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-710ad3062e7844aeb020b8259f2007b3
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09150555B2

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