Methyl iodide → Isoflavone

HRID 402861

反応式

HRID 402861 の反応式
[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

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 5280961Genistein

生成物 1

HCID 72304Isoflavone収率 65.7%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-183c03df9a044d8fa716ee0031b12092
出典データセット
uspto-grants-2014_06
特許番号
US08742141B2

関連ノート

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