Fluorene-2-carboxaldehyde → 2-vinylfluorene

HRID 436394

반응식

HRID 436394 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-vinylfluorene

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 1 1/2 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-10324234b1f54679ae0cd77a3b39a8ac
출처 데이터셋
uspto-grants-1977_02
특허 번호
US04009151

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