3-Acetylbenzonitrile → 3-Isopropenylbenzonitrile

HRID 1784944

반응식

HRID 1784944 반응식
[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]

참가 물질

5

반응물 2

HCID 802223-AcetylbenzonitrileHCID 178418339Butyllithium

생성물 1

HCID 121802503-Isopropenylbenzonitrile수율 86%

시약·촉매·용매 2

HCID 74505Methyltriphenyliphosphonium bromide촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e1d1ebcc11454a64b93acbc82c01bed0
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07504420B2

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