Hexane → 9-Methylene-9H-fluorene

HRID 742471

반응식

HRID 742471 반응식
[CH2:1]([Li])CCC.CCCCCC.[CH:12]1[C:24]2[C:23](=O)[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]=2[CH:15]=[CH:14][CH:13]=1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCOCC.O1CCCC1>[CH2:1]=[C:23]1[C:22]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:16]2[C:24]1=[CH:12][CH:13]=[CH:14][CH:15]=2

참가 물질

7

반응물 3

HCID 8058HexaneHCID 10241FluorenoneHCID 178418339Butyllithium

생성물 1

HCID 781479-Methylene-9H-fluorene수율 76.3%

시약·촉매·용매 3

HCID 74505Methyltriphenyliphosphonium bromide촉매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

A suspension of methyl triphenylphosphonium bromide (31.22 g; 87.3 mmol) in 500 mL of ether was added at -30° C. 10M n-butyllithium in hexane (8.73 mL; 87.3 mmol) and the mixture was allowed to stir at room temperature for 1/2 h. To the above mixture was added 15 g (83.2 mmol) of 9-fluorenone in 50 mL of tetrahydrofuran and the mixture was refluxed for 1 h. The above mixture was cooled to 0° C., filtered, and concentrated to yield 11.3 g (76.3%) of 9-methylene-fluorene (Formula III: R3 =R4 =H; R5 =R6 together form a 9-fluorene ring).

후처리

  1. additionwas added at -30° C
  2. temperaturethe mixture was refluxed for 1 h
  3. temperatureThe above mixture was cooled to 0° C.
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-898a58f2a809496f93f0a2a98eaea946
출처 데이터셋
uspto-grants-1996_09
특허 번호
US05554620

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