4-Toluenesulfonyl chloride → 3-Fluoroprop-1-yl toluene-4-sulphonate

HRID 1426999ノート

反応式

HRID 1426999 の反応式
C(N(CC)CC)C.[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1.[F:19][CH2:20][CH2:21][CH2:22][OH:23].O1CCCC1>CN(C)C1C=CN=CC=1.C(OCC)(=O)C.O>[CH3:18][C:8]1[CH:13]=[CH:12][C:11]([S:14]([O:23][CH2:22][CH2:21][CH2:20][F:19])(=[O:16])=[O:15])=[CH:10][CH:9]=1

参加物

8

反応物 4

HCID 73974-Toluenesulfonyl chlorideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 680423-Fluoro-1-propanol

生成物 1

HCID 63667743-Fluoroprop-1-yl toluene-4-sulphonate収率 85.4%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Triethylamine (11 mL, 79.4 mmol), 4-dimethylaminopyridine (390 mg, 3.19 mmol), and p-toluenesulfonyl chloride (13.4 g, 70.4 mmol) were added to a mixture of commercially available 3-fluoropropan-1-ol (5.0 g, 64 mmol) and tetrahydrofuran (120 mL) under nitrogen atmosphere at 0° C., and the mixture was stirred at mom temperature for 90 hours. Water and ethyl acetate were added to the reaction mixture for partition. The organic layer was washed with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and filtered. The solvent was evaporated, the resultant residue was dissolved in dichloromethane and n-heptane, and the resultant was purified with silica gel column chromatography (n-heptane:ethyl acetate=10:1-2:1) to obtain the title compound (12.7 g, 85%).

後処理

  1. customfor partition
  2. washThe organic layer was washed with water
  3. dry with materiala saturated saline solution, dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was evaporated
  6. dissolutionthe resultant residue was dissolved in dichloromethane
  7. customn-heptane, and the resultant was purified with silica gel column chromatography (n-heptane:ethyl acetate=10:1-2:1)

出典と根拠

ORDレコード
ord-8ccc62cf18914ea49310ce1f325ecf82
出典データセット
uspto-grants-2015_01
特許番号
US08933099B2

反応ノート

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