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

HRID 1042601ノート

反応式

HRID 1042601 の反応式
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

参加物

6

反応物 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 574219633-(2-Furyl)-1-(3,4,5-trimethoxyphenyl)prop-2-yn-1-oneHCID 687733295-Iodo-5-methoxyphenol

生成物 1

HCID 115605482-(2-Furyl)-6-methoxy-3-(3,4,5-trimethoxybenzoyl)benzo[b]furan収率 12%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
102.5 °C

実験手順

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)+.

後処理

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

出典と根拠

ORDレコード
ord-862199ffe3c44688aca21f8cb5b4de27
出典データセット
uspto-grants-2013_10
特許番号
US08557982B2

反応ノート

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