Triethylamine → 3-Methanesulfonyl-pyridine

HRID 902007ノート

反応式

HRID 902007 の反応式
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.C([Mg]Cl)(C)C.C(N(CC)CC)C.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>C1COCC1.O>[CH3:20][S:21]([C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1)(=[O:23])=[O:22]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 122863-BromopyridineHCID 31297Methanesulfonyl chlorideHCID 178418918HCID 178418918、化合物

生成物 1

HCID 4168063-Methanesulfonyl-pyridine

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 3-bromopyridine (20 g, 127 mmol) in THF (200 ml) at room temperature is added a solution of 2M isopropylmagnesium chloride in THF (64 ml, 127 mmol). The resulting mixture is stirred for 2 hours, treated with triethylamine (20 ml), immediately followed by methanesulfonylchloride (10 ml, 127 mmol) and the resulting mixture stirred for 18 hours at room temperature. The mixture is diluted with water (200 ml) and extracted with EtOAc (3×100 ml). The mixture is concentrated in vacuo and purified on Silica gel (eluting with 50/50 Hexane/EtOAc). 1H-NMR (CDCl3) δ: 9.17 (s, 1H), 8.90 (d, 1H), 8.25 (dd, 1H), 7.55 (m, 1H), 3.12 (s, 3H).

後処理

  1. stirringthe resulting mixture stirred for 18 hours at room temperature
  2. extractionextracted with EtOAc (3×100 ml)
  3. concentrationThe mixture is concentrated in vacuo
  4. custompurified on Silica gel (eluting with 50/50 Hexane/EtOAc)

出典と根拠

ORDレコード
ord-61df36c7a60b44f5a29b7362d13e19de
出典データセット
uspto-grants-2008_04
特許番号
US07365066B2

反応ノート

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