Fluorene-2-carboxaldehyde → 2-vinylfluorene

HRID 596544

反応式

HRID 596544 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

HCID 110416072-vinylfluorene

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0da5f13a5e9a40c78ab8d905c83a7eb5
出典データセット
uspto-grants-1977_03
特許番号
US04011266

関連ノート

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