Sodium Carbonate → 2-(2-Furyl)-6-methoxy-3-(3,4,5-trimethoxybenzoyl)benzo[b]furan

HRID 1042601Notes

Reaction equation

I[C:2]1([O:9][CH3:10])[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][CH2:3]1.[O:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[C:16]#[C:17][C:18]([C:20]1[CH:25]=[C:24]([O:26][CH3:27])[C:23]([O:28][CH3:29])=[C:22]([O:30][CH3:31])[CH:21]=1)=[O:19].[Li+].[Cl-].C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C>[O:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[C:16]1[O:8][C:6]2[CH:7]=[C:2]([O:9][CH3:10])[CH:3]=[CH:4][C:5]=2[C:17]=1[C:18](=[O:19])[C:20]1[CH:25]=[C:24]([O:26][CH3:27])[C:23]([O:28][CH3:29])=[C:22]([O:30][CH3:31])[CH:21]=1

Participants

Conditions

Temperature: 102.5 °C

Procedure

5-Iodo-5-methoxyphenol (125 mg, 0.5 mmol), 3-(2-furyl)-1-(3,4,5-trimethoxyphenyl)-prop-2-yn-1-one (172 mg, 0.6 mmol), LiCl (21.2 mg, 0.5 mmol) and Na2CO3 (265 mg, 2.5 mmol) were added to anhydrous DMF (3 ml) and flushed with N2 three times. Pd(OAc)z was added to the reaction mixture and again flushed with N2. The reaction mixture was heated to 100-105° C. for 6 h and then reaction was cooled to room temp. Quenched by addition of aqueous NH4Cl solution and extracted with EtOAc. 2-(2-Furyl)-6-methoxy-3-(3,4,5-trimethoxybenzoyl)benzo[b]furan was isolated in 12% yield by silica gel column chromatography using 20 to 40% EtOAc in hexane. 1H NMR (300 MHz, CDCl3) δ: 3.75 (s, 6H, OMe), 3.86 (s, 3H, OMe), 3.90 (s, 3H, OMe), 6.44-6.46 (m, 1H), 6.87 (dd, J=2.1, 8.7, 1H), 6.97 (d, J=3.6, 1H), 7.07 (d, J=2.1, 1H), 7.15 (s, 2H), 7.36 (d, J=8.7, 1H), 7.41 (d, J=1.2, 1H). MS (ES) m/z: 408.9 (M+H)+.

Workup

customflushed with N2 three times
additionPd(OAc)z was added to the reaction mixture
customagain flushed with N2
customreaction
temperaturewas cooled to room temp
customQuenched by addition of aqueous NH4Cl solution
extractionextracted with EtOAc

Sources & evidence

ORD record: ord-862199ffe3c44688aca21f8cb5b4de27
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08557982B2

Reaction notes

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