Hydrochloric Acid → 2-(4-Ethoxy-3,5-dimethoxyphenyl)furan

HRID 56548Notes

Reaction equation

[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([OH:14])=[C:8]([O:15][CH3:16])[CH:7]=1.C([O-])([O-])=O.[Cs+].[Cs+].I[CH2:24][CH3:25].Cl>CN(C=O)C.O.CCOC(C)=O>[CH2:24]([O:14][C:9]1[C:8]([O:15][CH3:16])=[CH:7][C:6]([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)=[CH:11][C:10]=1[O:12][CH3:13])[CH3:25]

Participants

Conditions

Temperature: 80 °C

Procedure

To a suspension of 4-(furan-2-yl)-2,6-dimethoxyphenol (0.493 g, 2.24 mmol) in anhydr DMF (10 mL) under argon was added Cs2CO3 (1.2 g, 3.7 mmol) and iodoethane (0.22 mL, 2.7 mmol). The mixture was stirred for 20 min then heated at 80° C. for 2 hrs. After cooling to room temperature, the reaction was diluted with H2O and EtOAc then it was acidified with the addition of 6 M HCl. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organics were diluted with hexanes and washed with H2O and brine, dried over Na2SO4 and filtered through a pad of silica gel on Celite. The filtrate was concentrated in vacuo to give 2-(4-ethoxy-3,5-dimethoxyphenyl)furan as a beige solid (0.513 g, 92% yield). The product was used without further purification.

Workup

temperatureAfter cooling to room temperature
customThe layers were separated
extractionthe aqueous layer was extracted with EtOAc
additionThe combined organics were diluted with hexanes
washwashed with H2O and brine
dry with materialdried over Na2SO4
filtrationfiltered through a pad of silica gel on Celite
concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-66aa4619628e4a21a21fa746a9428854
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434707B2

Reaction notes

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