Pyridine → HCID 23126022, 화합물

HRID 132728

반응식

HRID 132728 반응식
[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

참가 물질

7

반응물 4

HCID 1049Pyridine2회HCID 7412Benzoyl chlorideHCID 62324Propionyl chlorideHCID 3450229H-Fluorene-9,9-dimethanol

생성물 1

HCID 23126022HCID 23126022, 화합물수율 79%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-9ecee5bddf50403e821309d6521d6031
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07388061B2

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