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

HRID 1748563ノート

反応式

HRID 1748563 の反応式
[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

参加物

7

反応物 4

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

生成物 1

HCID 866925085-Bromo-2-(3,6-dihydro-2H-pyran-4-yl)-3-methylpyridine収率 86.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-710ad3062e7844aeb020b8259f2007b3
出典データセット
uspto-grants-2015_10
特許番号
US09150555B2

反応ノート

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