Dimethylformamide → Benzaldehyde, 2-(3-butenyl)-

HRID 921197노트

반응식

HRID 921197 반응식
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][CH:10]=[CH2:11].[Li]CCCC.CN(C)[CH:19]=[O:20]>C1COCC1>[CH2:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH:19]=[O:20])[CH2:9][CH:10]=[CH2:11]

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 34857122-(But-3-en-1-yl)bromobenzeneHCID 178418339Butyllithium

생성물 1

HCID 10261375Benzaldehyde, 2-(3-butenyl)-수율 92.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a mixture of 1-bromo-2-(but-3-en-1-yl)benzene (1 g, 4.74 mmol) in THF (10 mL) at −78° C. was added BuLi (2.274 mL, 5.68 mmol) dropwise. It was then stirred at this temperature for 1 h, then N,N-dimethylformamide (0.416 g, 5.68 mmol) was added. The reaction was stirred at 78° C. for 30 min, then warmed to rt and stirred at rt for 1 h. It was then quenched with NH4Cl, extracted with ether. The organic layer was then dried over MgSO4, filtered and concentrated. The residue was purified by biotage, eluting with 10% EtOAc/hexane to obtain 2-(but-3-en-1-yl)benzaldehyde (0.7 g, 92%) as an oil. 1H NMR (400 MHz, CDCl3) δ 10.35-10.26 (m, 1H), 7.86 (dd, J=7.6, 1.5 Hz, 1H), 7.54 (td, J=7.5, 1.6 Hz, 1H), 7.44-7.38 (m, 1H), 7.30 (d, J=8.1 Hz, 1H), 5.95-5.83 (m, 1H), 5.09-5.00 (m, 2H),), 3.20-3.12 (m, 2H), 2.44-2.36 (m, 2H).

후처리

  1. stirringThe reaction was stirred at 78° C. for 30 min
  2. stirringstirred at rt for 1 h
  3. customIt was then quenched with NH4Cl
  4. extractionextracted with ether
  5. dry with materialThe organic layer was then dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by biotage
  9. washeluting with 10% EtOAc/hexane

출처 및 근거

ORD 기록
ord-e27700a3db974338b81185866d2d5676
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09273067B2

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