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

HRID 1042601노트

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HRID 1042601 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
102.5 °C

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-862199ffe3c44688aca21f8cb5b4de27
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08557982B2

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