Pyridine → (R)-2-Hydroxy-2-(6-(trifluoromethyl)pyridin-3-yl)ethyl 4-methylbenzenesulfonate

HRID 1845120ノート

反応式

HRID 1845120 の反応式
[F:1][C:2]([F:14])([F:13])[C:3]1[N:8]=[CH:7][C:6]([C@@H:9]([OH:12])[CH2:10][OH:11])=[CH:5][CH:4]=1.N1C=CC=CC=1.[C:21]1([CH3:31])[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1>C(Cl)Cl>[CH3:31][C:21]1[CH:26]=[CH:25][C:24]([S:27]([O:11][CH2:10][C@H:9]([OH:12])[C:6]2[CH:7]=[N:8][C:3]([C:2]([F:13])([F:1])[F:14])=[CH:4][CH:5]=2)(=[O:29])=[O:28])=[CH:23][CH:22]=1

参加物

5

反応物 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 58188353(R)-1-(6-(Trifluoromethyl)pyridin-3-yl)ethane-1,2-diol

生成物 1

HCID 86652106(R)-2-Hydroxy-2-(6-(trifluoromethyl)pyridin-3-yl)ethyl 4-methylbenzenesulfonate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a stirred solution of (R)-1-(6-(trifluoromethyl)pyridin-3-yl)ethane-1,2-diol (6.4 g, 31 mmol) and pyridine (20 mL) in CH2Cl2 (200 mL) at 0° C. was added p-toluenesulfonyl chloride (7.0 g, 37 mmol) in small portions. The mixture was slowly warmed to rt and stirred for 40 hours, and then diluted with CH2Cl2 (100 mL). The organic phase was washed with aq. NaHCO3, brine, and dried (Na2SO4), and concentrated to yield the crude title compound.

後処理

  1. washThe organic phase was washed with aq. NaHCO3, brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated

出典と根拠

ORDレコード
ord-5509d6e88b324b4f911c6c1da21dc4cc
出典データセット
uspto-grants-2015_02
特許番号
US08946439B2

反応ノート

読み込み中…