Methyl iodide → Isoflavone

HRID 402861

반응식

HRID 402861 반응식
[CH:1]1[C:6]([C:7]2[C:16](=[O:17])[C:15]3[C:14](O)=[CH:13][C:12](O)=[CH:11][C:10]=3[O:9][CH:8]=2)=[CH:5][CH:4]=[C:3](O)[CH:2]=1.C([O-])([O-])=O.[K+].[K+].CI>CC(C)=O>[O:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:16](=[O:17])[C:7]([C:6]2[CH:1]=[CH:2][CH:3]=[CH:4][CH:5]=2)=[CH:8]1

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 5280961Genistein

생성물 1

HCID 72304Isoflavone수율 65.7%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

Prepared according to the general procedure using genistein (500 mg, 1.85 mmol), K2CO3 (1.02 g, 7.4 mmol), acetone (15 mL) and MeI (0.277 mL). Purified by flash column chromatography (SiO2, 10% EtOAc/Hex) to afford 16 (270 mg, 49%) as an off-white solid. Analytical data for isoflavone 16: 1H NMR (500 MHz, CDCl3) δ 12.88 (s, 1H), 7.88 (s, 1H), 7.48 (d, J=8.5 Hz, 2H), 7.00 (d, J=9 Hz, 2H), 6.41 (d, J=8.5 Hz, 2H), 3.89 (s, 3H), 3.86 (s, 3H); 13C NMR (125 MHz, CDCl3) δ 181.1, 165.8, 163.0, 160.0, 158.2, 152.9, 130.4, 123.9, 123.2, 114.3, 106.5, 98.4, 92.7, 56.1, 55.6; LCMS: Mass calculated for C17H14O5, [M+H]+, 299. Found 299.

후처리

  1. customPrepared
  2. customPurified by flash column chromatography (SiO2, 10% EtOAc/Hex)

출처 및 근거

ORD 기록
ord-183c03df9a044d8fa716ee0031b12092
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08742141B2

연결된 노트

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