4-Toluenesulfonyl chloride → 2-Fluoroethyl p-Toluenesulfonate

HRID 599191

反応式

HRID 599191 の反応式
[F:1][CH2:2][CH2:3][OH:4].[S:5](Cl)([C:8]1[CH:14]=[CH:13][C:11]([CH3:12])=[CH:10][CH:9]=1)(=[O:7])=[O:6]>N1C=CC=CC=1>[CH3:12][C:11]1[CH:13]=[CH:14][C:8]([S:5]([O:4][CH2:3][CH2:2][F:1])(=[O:7])=[O:6])=[CH:9][CH:10]=1

参加物

4

反応物 2

HCID 73974-Toluenesulfonyl chlorideHCID 97372-Fluoroethanol

生成物 1

HCID 2560192-Fluoroethyl p-Toluenesulfonate収率 95%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
0 °C

実験手順

To a 0° C. solution of 2-fluoroethanol (1.0 g, 15.6 mmol) in pyridine (15 mL) was added tosyl chloride (6.5 g, 34.1 mmol) over 30 min. The reaction mixture was stirred at 0° C. for 4 h and quenched by adding ice-cold water and EtOAc. The layers separated and the organic layer was washed successively with water, 1M HCl (5×), saturated Na2CO3 and brine. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was chromatographed on silica gel (12 g) using 5% to 40% EtOAc in hexane as the eluant to obtain fluorotosylate 20 (3.2 g, 95%) as a slightly yellow oil. 1H NMR (500 MHz, CDCl3) δ 7.83 (d, J=10.0 Hz, 1H), 7.38 (d, J=10.0 Hz, 2H), 4.59 (dt, J=50.0 & 5.0 Hz, 2H), 4.28 (dt, J=30.0 & 5.0 Hz, 2H), 2.47 (s, 3H).

後処理

  1. customquenched
  2. additionby adding ice-cold water and EtOAc
  3. customThe layers separated
  4. washthe organic layer was washed successively with water, 1M HCl (5×), saturated Na2CO3 and brine
  5. dry with materialThe organic layer was dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was chromatographed on silica gel (12 g)

出典と根拠

ORDレコード
ord-560ca48835c6429fb0777279549ea3de
出典データセット
uspto-grants-2011_03
特許番号
US07897769B2

関連ノート

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