Fluorene → 9,9-Bis(3,6-dioxaheptyl)-fluorene

HRID 1075373

반응식

HRID 1075373 반응식
C([Li])CCC.C1C2CC3C(=CC=CC=3)C=2C=CC=1.Cl[CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH3:26].[CH2:27]([CH:34]1[C:46]2[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=2[C:40]2[C:35]1=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH2:28][O:29][CH2:30][CH2:31][O:32][CH3:33]>CCCCCC.O1CCCC1.O>[CH2:20]([C:34]1([CH2:27][CH2:28][O:29][CH2:30][CH2:31][O:32][CH3:33])[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][C:40]=2[C:41]2[C:46]1=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH2:21][O:22][CH2:23][CH2:24][O:25][CH3:26]

참가 물질

8

반응물 4

HCID 6853FluoreneHCID 94934Ethane, 1-(2-chloroethoxy)-2-methoxy-2회HCID 541963909-[2-(2-Methoxyethoxy)ethyl]-9H-fluoreneHCID 178418339Butyllithium2회

생성물 1

HCID 178943479,9-Bis(3,6-dioxaheptyl)-fluorene

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매2회

반응 조건

온도
22 °C

실험 절차

7.05 g of butyllithium dissolved in 44 ml of hexane was slowly added in 5 minutes into 18.28 g of fluorene dissolved in 150 ml of anhydrous tetrahydrofuran at -50° C. under nitrogen protection. The mixture was stirred at -30~15° C. for 1 hour before it was cooled again to -40~-50° C. Then, 15.23 g of 1-chloro-2-(2-methoxyethoxy)-ethane was added in 5 minutes. The mixture was subsequently stirred for 2 hours while the temperature was gradually increased to 22° C. The main product in the solution was 9-(3,6-dioxaheptyl)-fluorene as detected by GC-MS. This solution was then cooled to -50° C., and 7.1 g of butyllithium dissolved in 44 ml of hexane was slowly added in 5 minutes under nitrogen protection. The mixture was stirred at -30 to -15° C. for 1 hour before it was cooled again to 40 to -50° C. Then, 15.30 g of 1-chloro-2-(2-methoxyethoxy)-ethane was added during 5 minutes. The mixture was subsequently stirred for 5 hours at 22° C., dispersed in water, and extracted with ether. The etheral solution was washed with water and brine, dried with magnesium sulfate, and evaporated. The residue was distilled to collect 37.1 g (91%) of colorless liquid at 160° C./0.08 mm Hg. MS (m/z): 370 (M+), 219, 191, 178, 89, 59.

후처리

  1. temperaturewas cooled again to -40~-50° C
  2. stirringThe mixture was subsequently stirred for 2 hours while the temperature
  3. temperatureThis solution was then cooled to -50° C.
  4. additionwas slowly added in 5 minutes under nitrogen protection
  5. stirringThe mixture was stirred at -30 to -15° C. for 1 hour before it
  6. temperaturewas cooled again to 40 to -50° C
  7. stirringThe mixture was subsequently stirred for 5 hours at 22° C.
  8. extractionextracted with ether
  9. washThe etheral solution was washed with water and brine
  10. dry with materialdried with magnesium sulfate
  11. customevaporated
  12. distillationThe residue was distilled
  13. customto collect 37.1 g (91%) of colorless liquid at 160° C./0.08 mm Hg

출처 및 근거

ORD 기록
ord-8051ec1713f648618766aa465c07f811
출처 데이터셋
uspto-grants-1999_05
특허 번호
US05900327

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