甲酸铵 → 4H-1-苯并吡喃-4-酮, 2,3-二氢-5,7-二羟基-3-(4-羟基苯基)-

HRID 449178

反应方程式

HRID 449178 反应方程式
[CH:1]1[C:6]([C:7]2[C:16](=[O:17])[C:15]3[C:14]([OH:18])=[CH:13][C:12]([OH:19])=[CH:11][C:10]=3[O:9][CH:8]=2)=[CH:5][CH:4]=[C:3]([OH:20])[CH:2]=1.C([O-])=O.[NH4+]>>[OH:18][C:14]1[CH:13]=[C:12]([OH:19])[CH:11]=[C:10]2[C:15]=1[C:16](=[O:17])[CH:7]([C:6]1[CH:5]=[CH:4][C:3]([OH:20])=[CH:2][CH:1]=1)[CH2:8][O:9]2

参与物

3

反应物 2

HCID 2723923甲酸铵HCID 5280961金雀异黄酮

产物 1

HCID 98383564H-1-苯并吡喃-4-酮, 2,3-二氢-5,7-二羟基-3-(4-羟基苯基)-收率 53%

实验过程

Compound 22 was prepared following the general procedure described by Wähälä K. and Hase T. A., Heterocycles 28:183-86 (1989), herein incorporated by reference in its entirety. To a 50 mL round bottom flask was added genistein (270 mg, 1 mmol) and ammonium formate (1.08 g, 4 mmol). The flask was purged with N2, followed by addition of methanol (20 mL) and 10% Pd/C (255 mg). Upon consumption of the starting material (measured by reverse phase HPLC), the reaction mixture was passed through a pad of silica gel with EtOAc/Hex as the eluent. The solvent was concentrated in vacuo to afford crude 22. Purified by recrystallization from CHCl3/MeOH to afford 22 (144 mg, 53%) as brown crystals. Analytical data for isoflavanone 22: 1H NMR (500 MHz, DMSO) δ 12.19 (s, 1H), 10.84 (br s, 1H), 9.42 (br s, 1H), 7.08 (d, J=8.5 Hz, 2H), 6.73 (d, J=8.5 Hz, 2H), 5.91-5.90 (s, 2H), 4.53 (d, J=6.5 Hz, 2H), 4.00 (t, J=6.5 Hz, 1H); 13C NMR (125 MHz, DMSO) δ 197.6, 167.4, 164.6, 163.6, 157.4, 130.4, 126.3, 116.0, 102.5, 96.9, 95.5, 49.9; LCMS: Mass calculated for C15H12O5, [M+H]+, 273. Found 273.

后处理

  1. customCompound 22 was prepared
  2. customThe flask was purged with N2
  3. additionfollowed by addition of methanol (20 mL) and 10% Pd/C (255 mg)
  4. customUpon consumption of the starting material (measured by reverse phase HPLC)
  5. concentrationThe solvent was concentrated in vacuo
  6. customto afford crude 22
  7. customPurified by recrystallization from CHCl3/MeOH

来源与证据

ORD记录
ord-de3af3a06781475abde7cf4e47387010
来源数据集
uspto-grants-2013_07
专利号
US08481760B2

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