Hydrochloric Acid → HCID 46927722、化合物

HRID 573026

反応式

HRID 573026 の反応式
[CH2:1]([O:23][C:24]1[CH:36]=[CH:35][C:34]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27](=[O:37])[C:26]=2[CH:25]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].[Cl:38][C:39]1[CH:44]=[CH:43][C:42]([Mg]Br)=[CH:41][CH:40]=1.Cl>C1COCC1>[CH2:1]([O:23][C:24]1[CH:36]=[CH:35][C:34]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27]([C:42]3[CH:43]=[CH:44][C:39]([Cl:38])=[CH:40][CH:41]=3)([OH:37])[C:26]=2[CH:25]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 667190052-Docosyloxy-9-fluorenoneHCID 178478191HCID 178478191、化合物

生成物 1

HCID 46927722HCID 46927722、化合物収率 88%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Under a nitrogen atmosphere, 2-docosyloxy-9-fluorenone (250 mg, 0.50 mmol) prepared in the above-mentioned 1-1 was suspended in THF (2.5 ml), and dissolved at 50° C. 4-Chlorophenylmagnesium bromide solution was added dropwise, and the mixture was stirred. After completion of the reaction, the reaction mixture was cooled to room temperature, 1N hydrochloric acid was added dropwise thereto in a water bath until foaming stopped to quench the reaction. The mixture was extracted with chloroform (15 ml), and washed 3 times with 1N hydrochloric acid (5 ml), 3 times with 5% NaHCO3 solution (5 ml), and once with 20% NaCl solution (5 ml). The organic layer was dried over Na2SO4, and the solvent of the filtrate was evaporated. The obtained residue was isolated and purified by silica gel column chromatography, and precipitated with methanol (3 ml) to give 2-docosyloxy-9-(4-chlorophenyl)-9-fluorenol (270 mg, 0.44 mmol, 88%).

後処理

  1. dissolutiondissolved at 50° C
  2. customAfter completion of the reaction
  3. customin a water bath until foaming stopped
  4. customto quench
  5. customthe reaction
  6. extractionThe mixture was extracted with chloroform (15 ml)
  7. washwashed 3 times with 1N hydrochloric acid (5 ml), 3 times with 5% NaHCO3 solution (5 ml)
  8. dry with materialThe organic layer was dried over Na2SO4
  9. customthe solvent of the filtrate was evaporated
  10. customThe obtained residue was isolated
  11. custompurified by silica gel column chromatography
  12. customprecipitated with methanol (3 ml)

出典と根拠

ORDレコード
ord-ca260bee391248d687822c61a2672d76
出典データセット
uspto-grants-2015_05
特許番号
US09029504B2

関連ノート

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