Sodium Carbonate → HCID 22617308、化合物

HRID 841847ノート

反応式

HRID 841847 の反応式
[CH2:1]([O:3][CH2:4][CH:5]1[CH2:10][CH2:9][CH:8]([CH:11]2[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22](OS(C(F)(F)F)(=O)=O)=[CH:21][CH:20]=3)[CH2:13][CH2:12]2)[CH2:7][CH2:6]1)[CH3:2].OB(O)[C:35]1[CH:40]=[C:39]([F:41])[C:38]([O:42][C:43]([F:46])([F:45])[F:44])=[C:37]([F:47])[CH:36]=1.C(=O)([O-])[O-].[Na+].[Na+]>[Pd].O>[CH2:1]([O:3][CH2:4][CH:5]1[CH2:10][CH2:9][CH:8]([CH:11]2[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([C:35]4[CH:40]=[C:39]([F:41])[C:38]([O:42][C:43]([F:46])([F:45])[F:44])=[C:37]([F:47])[CH:36]=4)=[CH:21][CH:20]=3)[CH2:13][CH2:12]2)[CH2:7][CH2:6]1)[CH3:2]

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 23443787B-[3,5-Difluoro-4-(trifluoromethoxy)phenyl]boronic acidHCID 54072023HCID 54072023、化合物

生成物 1

HCID 22617308HCID 22617308、化合物

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 962Water溶媒

実験手順

6.3 g (13 mmol) of 4-(2-(4-(4-ethoxymethylcyclohexyl) cyclohexyl) ethyl) trifluoromethylsulfonyloxybenzene, 4.2 g (17 mmol) of dihydroxy (3,5-difluoro-4-trifluoromethoxyphenyl) borane, 5% palladium on activated charcoal (1.0 g) and 5.7 g (54 mmol) of sodium carbonate were refluxed in toluene/alcohol/water (1/1/1 v/v, 80 ml) under a nitrogen atmosphere for 3 days. After cooling, the reaction solution was added with water (150 ml) and extracted twice with toluene (150 ml). An organic layer was dried over anhydrous magnesium sulfate, filtered and the solvent therein was distilled off under a reduced pressure. The residue thus obtained was purified by column chromatography (silica gel/heptane:toluene=5:1) and recrystallization (heptane-ethanol) to obtain colorless crystals of 4-(4-(2-(4-(4-ethoxymethylcyclohexyl)cyclohexyl)ethyl)phenyl)-2,6-difluorotrifluoromethoxybenzene.

後処理

  1. temperatureAfter cooling
  2. extractionextracted twice with toluene (150 ml)
  3. dry with materialAn organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. distillationthe solvent therein was distilled off under a reduced pressure
  6. customThe residue thus obtained
  7. customwas purified by column chromatography (silica gel/heptane:toluene=5:1) and recrystallization (heptane-ethanol)

出典と根拠

ORDレコード
ord-c1b6d4f3fe404ff78aa7c7a1464c192a
出典データセット
uspto-grants-2002_04
特許番号
US06372153B1

反応ノート

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