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

HRID 921197ノート

反応式

HRID 921197 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e27700a3db974338b81185866d2d5676
出典データセット
uspto-grants-2016_03
特許番号
US09273067B2

反応ノート

読み込み中…