醋酸 → 3,5-Diethoxy-4-pyrrol-1-yl-benzoic acid ethyl ester

HRID 1715144

反应方程式

HRID 1715144 反应方程式
[CH2:1]([O:3][C:4](=[O:18])[C:5]1[CH:10]=[C:9]([O:11][CH2:12][CH3:13])[C:8]([NH2:14])=[C:7]([O:15][CH2:16][CH3:17])[CH:6]=1)[CH3:2].C(O)(=O)C.CO[CH:25]1[CH2:29][CH2:28][CH:27](OC)O1>CCCCCCC>[CH2:1]([O:3][C:4](=[O:18])[C:5]1[CH:10]=[C:9]([O:11][CH2:12][CH3:13])[C:8]([N:14]2[CH:25]=[CH:29][CH:28]=[CH:27]2)=[C:7]([O:15][CH2:16][CH3:17])[CH:6]=1)[CH3:2]

参与物

5

反应物 3

HCID 176醋酸HCID 790982,5-二甲氧基四氢呋喃HCID 123984444-Amino-3,5-diethoxybenzoic acid ethyl ester

产物 1

HCID 669121583,5-Diethoxy-4-pyrrol-1-yl-benzoic acid ethyl ester收率 82%

试剂、催化剂与溶剂 1

HCID 8900庚烷溶剂

实验过程

To a solution of 4-amino-3,5-diethoxy-benzoic acid ethyl ester (3.0 g, 11.84 mmol, 1.0 equiv; prepared as described in I. Kompis and A. Wick, Helv. Chim. Acta 1977, 60, 3025-3034) in heptane (10 mL) and conc. acetic acid (0.2 mL) was added 2,5-dimethoxy-tetrahydro-furan (1.88 g, 14.21 mmol, 1.2 equiv). After heating to reflux for 5 h, a Dean-Stark apparatus was attached and the reaction mixture heated for an additional time period of 5 h. Filtration of the crude reaction mixture and crystallization at 0° C. from heptane provided 2.94 g (82%) of the title compound. 1H NMR (300 MHz, DMSO): δ 1.15 (t, J=7.0 Hz, 6H), 1.27 (t, J=7.1 Hz, 3H), 3.98 (q, J=7.0 Hz, 4H), 4.28 (q, J=7.1 Hz, 2H), 6.07-6.08 (m, 2H), 6.73-6.74 (m, 2H), 7.22 (s, 2H). 13C NMR (75 MHz, DMSO): δ 14.11, 14.35, 61.06, 64.57, 106.87, 107.64, 122.61, 123.33, 129.29, 153.75, 165.06. MS (ISP): 303.4 [M+H]+.

后处理

  1. customprepared
  2. temperatureAfter heating
  3. temperatureto reflux for 5 h
  4. temperaturethe reaction mixture heated for an additional time period of 5 h
  5. filtrationFiltration of the crude
  6. customreaction mixture and crystallization at 0° C. from heptane

来源与证据

ORD记录
ord-1e4babf3052940d9a46bdd1fb3052494
来源数据集
uspto-grants-2010_09
专利号
US07799806B2

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