Trifluoroacetic anhydride → Triphenylsulfonium 2-(adamantane-1-carbonyloxy)ethanesulfonate

HRID 1943564ノート

反応式

HRID 1943564 の反応式
[S:1]([CH2:5][CH2:6][OH:7])([O-:4])(=[O:3])=[O:2].[Na+].[C:9]12([C:19](O)=[O:20])[CH2:18][CH:13]3[CH2:14][CH:15]([CH2:17][CH:11]([CH2:12]3)[CH2:10]1)[CH2:16]2.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[Cl-].[C:36]1([S+:42]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C(=O)(O)[O-].[Na+]>FC(F)(F)C(O)=O.C(Cl)Cl.O>[C:9]12([C:19]([O:7][CH2:6][CH2:5][S:1]([O-:4])(=[O:3])=[O:2])=[O:20])[CH2:16][CH:15]3[CH2:14][CH:13]([CH2:12][CH:11]([CH2:17]3)[CH2:10]1)[CH2:18]2.[C:49]1([S+:42]([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=1

参加物

9

反応物 5

HCID 9845Trifluoroacetic anhydrideHCID 132351-Adamantanecarboxylic acidHCID 61343Triphenylsulfonium chlorideHCID 516892Sodium BicarbonateHCID 517063Sodium Isethionate

生成物 1

HCID 86642232Triphenylsulfonium 2-(adamantane-1-carbonyloxy)ethanesulfonate収率 62%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 6422Trifluoroacetic acid溶媒

実験手順

In 125 g of trifluoroacetic acid were dissolved 14.8 g (0.10 mole) of sodium isethionate and 18.0 g (0.10 mole) of 1-adamantanecarboxylic acid. To this solution, 32.0 g (0.15 mole) of trifluoroacetic anhydride was added dropwise, followed by stirring for 2 hours at room temperature. Then 430 g (0.15 mole) of an aqueous solution of triphenylsulfonium chloride prepared in Synthesis Example 1-1, 800 g of water, and 1,500 g of methylene chloride were added, followed by stirring for 1 hour at room temperature. At the end of stirring, the organic layer was taken out, aqueous sodium bicarbonate was added dropwise until the pH of the aqueous layer ceased to be acidic, and the organic layer was then taken out. The organic layer was washed with water and concentrated in vacuum. Methyl isobutyl ketone was added to the concentrate, which was concentrated in vacuum again while distilling off the residual water. Diisopropyl ether was added to the residue for recrystallization. The crystals were collected and dried, obtaining the target compound, triphenylsulfonium 2-(adamantane-1-carbonyloxy)ethanesulfonate. White crystals, 34.1 g, yield 62%. The compound, designated PAG-1, has the following structure.

後処理

  1. additionwere added
  2. stirringby stirring for 1 hour at room temperature
  3. stirringAt the end of stirring
  4. washThe organic layer was washed with water
  5. concentrationconcentrated in vacuum
  6. additionMethyl isobutyl ketone was added to the concentrate, which
  7. concentrationwas concentrated in vacuum again
  8. distillationwhile distilling off the residual water
  9. additionDiisopropyl ether was added to the residue for recrystallization
  10. customThe crystals were collected
  11. customdried

出典と根拠

ORDレコード
ord-e594ef7332c24e08b2be557c4bd48e27
出典データセット
uspto-grants-2013_03
特許番号
US08394570B2

反応ノート

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