Diisobutylaluminumhydride → (3,5-Diethoxy-4-pyrrol-1-yl-phenyl)-methanol

HRID 913314

反应方程式

HRID 913314 反应方程式
C([O:3][C:4](=O)[C:5]1[CH:10]=[C:9]([O:11][CH2:12][CH3:13])[C:8]([N:14]2[CH:18]=[CH:17][CH:16]=[CH:15]2)=[C:7]([O:19][CH2:20][CH3:21])[CH:6]=1)C.[H-].C([Al+]CC(C)C)C(C)C>C1(C)C=CC=CC=1>[CH2:20]([O:19][C:7]1[CH:6]=[C:5]([CH2:4][OH:3])[CH:10]=[C:9]([O:11][CH2:12][CH3:13])[C:8]=1[N:14]1[CH:15]=[CH:16][CH:17]=[CH:18]1)[CH3:21]

参与物

4

反应物 2

HCID 21225700DiisobutylaluminumhydrideHCID 669121583,5-Diethoxy-4-pyrrol-1-yl-benzoic acid ethyl ester

产物 1

HCID 66912179(3,5-Diethoxy-4-pyrrol-1-yl-phenyl)-methanol收率 100%

试剂、催化剂与溶剂 1

HCID 1140甲苯溶剂

实验过程

To a solution of 3,5-diethoxy-4-pyrrol-1-yl-benzoic acid ethyl ester (1.51 g, 4.98 mmol, 1.0 equiv) in toluene (5 mL) was added slowly over a time period of 15 min under slight cooling to 20° C. a solution of diisobutylaluminum hydride (8.9 mL, 12.45 mmol, 2.5 equiv; 20% solution in toluene). After 1 h, the excess of hydride was quenched by cautious addition of water (10 mL) and a 28% solution of NaOH (2 mL). The mixture was stirred for 30 min and the organic phase filtered over Hyflo Super Cel. The aqueous layer was extracted with toluene (2×50 mL), the combined organic phases washed with a sat. solution of NaCl (2×50 mL) and concentrated by evaporation under reduced pressure to afford 1.30 g (100%) of (3,5-diethoxy-4-pyrrol-1-yl-phenyl)-methanol. The crude alcohol (1.30 g, 4.98 mmol, 1.0 equiv) was dissolved in toluene (20 mL), and activated MnO2 (7.79 g, 89.5 mmol, 18.0 equiv) was added. The reaction mixture was heated to reflux for 7 h, after which time the reaction mixture was filtered through Hyflo Super Cel and concentrated yielding 1.15 g (89% yield) of the title compound. 1H NMR (300 MHz, DMSO): δ 1.17 (t, J=7.0 Hz, 6H), 4.02 (q, J=7.0 Hz, 4H), 6.08-6.09 (m, 2H), 6.75-6.76 (m, 2H), 7.25 (s, 2H), 9.89 (s, 1H). MS (ISP): 260.1 [M+H]+.

后处理

  1. customthe excess of hydride was quenched by cautious addition of water (10 mL)
  2. filtrationthe organic phase filtered over Hyflo Super Cel
  3. extractionThe aqueous layer was extracted with toluene (2×50 mL)
  4. washthe combined organic phases washed with a sat. solution of NaCl (2×50 mL)
  5. concentrationconcentrated by evaporation under reduced pressure

来源与证据

ORD记录
ord-020623662adb4083b0ee4cd50b4d7b6c
来源数据集
uspto-grants-2011_09
专利号
US08026365B2

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