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

HRID 502372

反应方程式

HRID 502372 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) in toluene (5 mL) was added slowly over a time period of 15 min under slight cooling to 20° C. a solution of diisobutylaluminium hydride (8.9 mL, 12.45 mmol, 20% solution in toluene). After 1 h, the excess hydride was quenched by cautious addition of water (10 mL) and a 28% solution of sodium hydoxide (2 mL). The mixture was stirred for 30 min and the organic phase filtered over Hyflo. The aqueous layer was extracted with toluene (2×50 mL), the combined organic phases washed with a sat. solution of sodium chloride (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 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 was filtered through Hyflo and concentrated yielding 1.15 g (89% yield) of the title compound.

后处理

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

来源与证据

ORD记录
ord-5dc572e3304648388b9b5c1bc66aff34
来源数据集
uspto-grants-2010_08
专利号
US07772253B2

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