Pyridine → HCID 23126022、化合物

HRID 132728

反応式

HRID 132728 の反応式
[OH:1][CH2:2][C:3]1([CH2:16][OH:17])[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2.N1C=CC=CC=1.[C:24](Cl)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[C:33](Cl)(=[O:36])[CH2:34][CH3:35]>O.O1CCCC1>[C:24]([O:1][CH2:2][C:3]1([CH2:16][O:17][C:33](=[O:36])[CH2:34][CH3:35])[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

参加物

7

反応物 4

HCID 1049Pyridine2 回HCID 7412Benzoyl chlorideHCID 62324Propionyl chlorideHCID 3450229H-Fluorene-9,9-dimethanol

生成物 1

HCID 23126022HCID 23126022、化合物収率 79%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To 4.5 g (0.02 mol) 9,9-di(hydroxymethyl)fluorene were added 30 ml tetrahydrofuran, and added 3.3 ml (0.03 mol) pyridine with stirring. To the resulting homogenous mixture was added slowly 2.3 ml (0.02 mol) benzoyl chloride, and the mixture was stirred at temperature for 1 hour, then heated refluxing for 5 hours. Next, the mixture was cooled to room temperature, and 20 ml tetrahydrofuran and 3.3 ml(0.03 mol) pyridine were added with stirring. To the resulting homogenous mixture was slowly added 1.8 ml (0.02 mol) propionyl chloride, and the mixture was stirred at room temperature for 1 hour, and heated refluxing for 5 hours. Then 30 ml water was added to dissolve the resulting salt. The mixture was extracted with toluene. The organic phase was separated, washed with saturated saline for two times, and dried over anhydrous sodium sulfate. The solvent was removed. Recrystallization from ethyl acetate gave 9-(benzoyloxymethyl)-9-(propionyloxymethyl)fluorene as a white crystal, and the yield was 79%. 1HNMR: δ (ppm) 1.23(t, 3H, CH3), 2.39(m, 2H, CH2), 4.48(s, 2H, COOCH2), 4.62(s, 2H, OCH2 linking with benzoyl), 7.33-8.03(m, 13H, ArH)

後処理

  1. stirringthe mixture was stirred at temperature for 1 hour
  2. temperatureheated
  3. temperaturerefluxing for 5 hours
  4. stirringwith stirring
  5. stirringthe mixture was stirred at room temperature for 1 hour
  6. temperatureheated
  7. temperaturerefluxing for 5 hours
  8. dissolutionto dissolve the resulting salt
  9. extractionThe mixture was extracted with toluene
  10. customThe organic phase was separated
  11. washwashed with saturated saline for two times
  12. dry with materialdried over anhydrous sodium sulfate
  13. customThe solvent was removed
  14. customRecrystallization from ethyl acetate

出典と根拠

ORDレコード
ord-9ecee5bddf50403e821309d6521d6031
出典データセット
uspto-grants-2008_06
特許番号
US07388061B2

関連ノート

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