3,4,5-Trimethoxybenzaldehyde → 3-(2-Furyl)-1-(3,4,5-trimethoxyphenyl)prop-2-yn-1-one

HRID 1042600노트

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HRID 1042600 반응식
[C:1]([C:3]1[O:4][CH:5]=[CH:6][CH:7]=1)#[CH:2].[Li]CCCC.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:20]=[C:21]([O:25][CH3:26])[C:22]=1[O:23][CH3:24])[CH:18]=[O:19]>C1COCC1>[O:4]1[CH:5]=[CH:6][CH:7]=[C:3]1[C:1]#[C:2][C:18]([C:17]1[CH:20]=[C:21]([O:25][CH3:26])[C:22]([O:23][CH3:24])=[C:15]([O:14][CH3:13])[CH:16]=1)=[O:19]

참가 물질

5

반응물 3

HCID 68583,4,5-TrimethoxybenzaldehydeHCID 140409Furan, 2-ethynyl-HCID 178418339Butyllithium

생성물 1

HCID 574219633-(2-Furyl)-1-(3,4,5-trimethoxyphenyl)prop-2-yn-1-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

2-Ethynylfuran (200 mg, 2.17 mmol) was dissolved in dry THF (10 ml) and cooled to −78° C. under N2 atmosphere. BuLi (1.2 ml, 2.4 mmol) was added slowly and stirred at −78° C. for 10 min and then 3,4,5-trimethoxybenzaldehyde (500 mg, 2.6 mmol) was added and reaction mixture was stirred for 1 h at −78° C. and then reaction temp raised to room temp. The reaction was quenched by addition of aqueous NH4Cl solution and extracted with EtOAc. The colorless oil was dissolved in dichloromethane and excess of MnO2 was added to it and stirred overnight at room temp. The reaction mixture was filtered through celite plug and evaporated to dryness. 3-(2-furyl)-1-(3,4,5-trimethoxyphenyl)prop-2-yn-1-one was precipitated from ether by slow addition of hexane as off-white powder (65%). 1H NMR (300 MHz, CDCl3) δ 3.93 (s, 9H), 6.50-6.52 (m, 1H), 7.01 (d, J=3.6 Hz, 1H), 7.45 (s, 2H), 7.24 (s, 1H), 7.55 (d, J=1.5 Hz).

후처리

  1. customreaction mixture
  2. stirringwas stirred for 1 h at −78° C.
  3. customreaction
  4. temperaturetemp raised to room temp
  5. customThe reaction was quenched by addition of aqueous NH4Cl solution
  6. extractionextracted with EtOAc
  7. dissolutionThe colorless oil was dissolved in dichloromethane and excess of MnO2
  8. additionwas added to it
  9. stirringstirred overnight at room temp
  10. filtrationThe reaction mixture was filtered through celite plug
  11. customevaporated to dryness
  12. custom3-(2-furyl)-1-(3,4,5-trimethoxyphenyl)prop-2-yn-1-one was precipitated from ether by slow addition of hexane as off-white powder (65%)

출처 및 근거

ORD 기록
ord-077b0e23ea9b4bdd83fed3acfe65f9a4
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08557982B2

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