Fluorene-2-carboxaldehyde → 2-ethenyl-9H-fluorene

HRID 596544

반응식

HRID 596544 반응식
[Br-].[C:2]1([C:8]([PH3+])([C:15]2C=CC=[CH:17][CH:16]=2)[C:9]2[CH:14]=CC=C[CH:10]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:22]([Li])[CH2:23]CC.C1C2CC3C(=CC=CC=3)C=2C=CC=1C=O>C1COCC1.CCCCCC>[CH:22]([C:17]1[CH:16]=[CH:15][C:8]2[C:2]3[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:14][C:9]=2[CH:10]=1)=[CH2:23]

참가 물질

6

반응물 3

HCID 34804Fluorene-2-carboxaldehydeHCID 21951224Triphenylmethyl phosphonium bromideHCID 178418339Butyllithium

생성물 1

HCID 110416072-ethenyl-9H-fluorene

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매2회

실험 절차

Triphenylmethyl phosphonium bromide (36 gms/0.1 mole) in 500 milliliters of dry THF is treated under nitrogen with 90 milliliters of a 1.1 molar solution of n-butyl lithium in hexane and stirred for 2 hours. A solution of 19.4 gms. (0.1 mole) of fluorene-2-carboxaldehyde in 100 milliliters of THF is added dropwise and the final mixture refluxed for 11/2 hours. One liter of hexane is added to the cold solution and the precipitate filtered off. The filtrate is evaporated and the residue chromatographed on alumina (Woehlm neutral) using hexane to give 15 gms. (75% theory) of product. Recrystallization from hexane yields 2-vinylfluorene as colorless plates. The structure of the product is confirmed by nuclear magnetic resonance and elemental analysis.

후처리

  1. filtrationthe precipitate filtered off
  2. customThe filtrate is evaporated
  3. customthe residue chromatographed on alumina (Woehlm neutral)
  4. customto give 15 gms
  5. customRecrystallization from hexane

출처 및 근거

ORD 기록
ord-0da5f13a5e9a40c78ab8d905c83a7eb5
출처 데이터셋
uspto-grants-1977_03
특허 번호
US04011266

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