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

HRID 1042600

Reaction equation

HRID 1042600 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

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).

Workup

  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%)

Sources & evidence

ORD record
ord-077b0e23ea9b4bdd83fed3acfe65f9a4
Source dataset
uspto-grants-2013_10
Patent number
US08557982B2

Linked notes

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