3-Acetylbenzonitrile → 3-Isopropenylbenzonitrile

HRID 1784944

反応式

HRID 1784944 の反応式
[Li][CH2:2]CCC.[C:6]([C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[C:12]#[N:13])(=O)[CH3:7]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[CH2:7]=[C:6]([C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[C:12]#[N:13])[CH3:2]

参加物

5

反応物 2

HCID 802223-AcetylbenzonitrileHCID 178418339Butyllithium

生成物 1

HCID 121802503-Isopropenylbenzonitrile収率 86%

試薬・触媒・溶媒 2

HCID 74505Methyltriphenyliphosphonium bromide触媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To the methyl triphenylphosphoniumbromide (4.3 grn, 12 mmol) in THF at 0° C., n-BuLi (1.6M, 7.5 ml, 12 mmol) was added and stirred for 30 min. Then 3-acetylbenzonitrile in THF was slowly added and the reaction mixture was stirred at 0° C. for further 3 h. Then reaction mixture was quenched with aqeous ammonium chloride and diluted with ethyl acetate. Organic layer was washed with water, brine and dried. Crude residue after column purification yielded 3-(prop-1-en-2-yl)benzonitrile in 86% yield.

後処理

  1. stirringthe reaction mixture was stirred at 0° C. for further 3 h
  2. customThen reaction mixture
  3. customwas quenched with aqeous ammonium chloride
  4. additiondiluted with ethyl acetate
  5. washOrganic layer was washed with water, brine
  6. customdried
  7. customCrude residue after column purification

出典と根拠

ORDレコード
ord-e1d1ebcc11454a64b93acbc82c01bed0
出典データセット
uspto-grants-2009_03
特許番号
US07504420B2

関連ノート

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