1-Propanesulfonic acid, 1,1,2,3,3,3-hexafluoro- → Tris-(4-hydroxyphenyl) sulfonium 3,3,3,2,1,1-hexafluoropropane sulfonate

HRID 277686ノート

反応式

HRID 277686 の反応式
[F:1][C:2]([F:13])([F:12])[CH:3]([F:11])[C:4]([F:10])([F:9])[S:5]([O-:8])(=[O:7])=[O:6].C(OC(C[O:22][C:23]1[CH:28]=[CH:27][C:26]([S+:29]([C:45]2[CH:50]=[CH:49][C:48]([O:51]CC(OC(C)(C)C)=O)=[CH:47][CH:46]=2)[C:30]2[CH:35]=[CH:34][C:33]([O:36]CC(OC(C)(C)C)=O)=[CH:32][CH:31]=2)=[CH:25][CH:24]=1)=O)(C)(C)C.FC(F)(F)C(F)C(F)(F)S(O)(=O)=O>C(O)C>[F:13][C:2]([F:1])([F:12])[CH:3]([F:11])[C:4]([F:9])([F:10])[S:5]([O-:8])(=[O:6])=[O:7].[OH:22][C:23]1[CH:28]=[CH:27][C:26]([S+:29]([C:45]2[CH:50]=[CH:49][C:48]([OH:51])=[CH:47][CH:46]=2)[C:30]2[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=2)=[CH:25][CH:24]=1

参加物

4

反応物 2

HCID 97946281-Propanesulfonic acid, 1,1,2,3,3,3-hexafluoro-HCID 88189193Tris-(4-t-butoxycarbonylmethoxyphenyl) sulfonium 3,3,3,2,1,1-hexafluoropropane sulfonate

生成物 1

HCID 88189245Tris-(4-hydroxyphenyl) sulfonium 3,3,3,2,1,1-hexafluoropropane sulfonate収率 100%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

56.8 g (0.08 mol) of tris-(4-butoxyphenyl) sulfonium 3,3,3,2,1,1-hexafluoropropane sulfonate (Synthesis Example 110) and 1.86 g (0.008 mol) of 3,3,3,2,1,1-hexafluoropropane sulfonic acid were dissolved in 200 ml of ethanol. The solution was heated under ref lux for 8 hours with stirring. After removal of the solvent by distillation, the obtained crude product of tris-(4-hydroxyphenyl) sulfonium 3,3,3,2,1,1-hexafluoropropane sulfonate (yield about 100%) was dissolved in 160 g of N,N-dimethylformamide and reacted with 55.4 g (0.40 mol) of anhydrous potassium carbonate and 60.3 g (0.40 mol) of di-t-butyl dicarbonate at 20° C. for 3 hours. The reaction solution was poured into 700 ml of water and extracted with dichloromethane. The organic phase was washed with water and dried. The solvent was removed by distillation. The oily residue was purified by column chromatography on silica gel using a dichloromethane and methanol as the developing solvent. The white product was collected to yield 31.8 g (yield 45%) of analytically pure tris-(4-t-butoxycarbonylmethoxyphenyl) sulfonium 3,3,3,2,1,1-hexafluoropropane sulfonate. The melting point of the product was 78° C. The 1H-NMR spectrum gave the following signals (CDCl3): δ=1.45 (s, 27H), 5.30-5.56 (d[m], 1H), 7.10-7.13 (d, 6H), 7.55-7.60 (d, 6H).

後処理

  1. temperatureThe solution was heated under ref lux for 8 hours
  2. customAfter removal of the solvent
  3. distillationby distillation

出典と根拠

ORDレコード
ord-9cf152e631114ce08dcef394758bc17c
出典データセット
uspto-grants-2002_03
特許番号
US06358665B1

反応ノート

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