Pyridine → Triphenylsulfonium 2-(2-chloroacetoxy)-1,1,3,3,3-pentafluoropropane-1-sulfonate

HRID 556242ノート

反応式

HRID 556242 の反応式
[OH:1][CH:2]([C:10]([F:13])([F:12])[F:11])[C:3]([F:9])([F:8])[S:4]([O-:7])(=[O:6])=[O:5].[C:14]1([S+:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Cl:33][CH2:34][C:35](Cl)=[O:36].N1C=CC=CC=1>C(#N)C>[Cl:33][CH2:34][C:35]([O:1][CH:2]([C:10]([F:13])([F:11])[F:12])[C:3]([F:8])([F:9])[S:4]([O-:7])(=[O:6])=[O:5])=[O:36].[C:27]1([S+:20]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

参加物

5

反応物 3

HCID 1049PyridineHCID 6577Chloroacetyl chlorideHCID 86612198HCID 86612198、化合物

生成物 1

HCID 86639508Triphenylsulfonium 2-(2-chloroacetoxy)-1,1,3,3,3-pentafluoropropane-1-sulfonate収率 92.6%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a mixture of 148 g (0.30 mole) of triphenylsulfonium 2-hydroxy-1,1,3,3,3-pentafluoropropane-1-sulfonate synthesized in Synthesis Example 1-11, 37.3 g (0.33 mole) of chloroacetyl chloride, and 600 g of acetonitrile, 28.5 g (0.36 mole) of pyridine was added dropwise, followed by stirring at room temperature for 3 hours. The reaction solution was then concentrated and combined with 300 g of 5% dilute hydrochloric acid and 600 g of dichloromethane whereupon the organic layer was separated. The organic layer was washed with 300 g of water, from which dichloromethane was distilled off under vacuum. To the residue was added 600 g of methyl isobutyl ketone. This was washed with 300 g of water, with 300 g of dilute aqueous ammonia, and three times with 300 g of water whereupon methyl isobutyl ketone was distilled off under vacuum. The residue was purified by adding ether for recrystallization, filtered and dried. The target compound was obtained as white crystals (158 g, yield 92%).

後処理

  1. additionwas added dropwise
  2. concentrationThe reaction solution was then concentrated
  3. customwas separated
  4. washThe organic layer was washed with 300 g of water, from which dichloromethane
  5. distillationwas distilled off under vacuum
  6. additionTo the residue was added 600 g of methyl isobutyl ketone
  7. washThis was washed with 300 g of water, with 300 g of dilute aqueous ammonia, and three times with 300 g of water whereupon methyl isobutyl ketone
  8. distillationwas distilled off under vacuum
  9. customThe residue was purified
  10. additionby adding ether
  11. customfor recrystallization
  12. filtrationfiltered
  13. customdried

出典と根拠

ORDレコード
ord-13125df7e05d4d28ac5168ff574b558f
出典データセット
uspto-grants-2011_11
特許番号
US08057985B2

反応ノート

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