3-Phenyl-2-triethylsilyl-4furaldehyde → 3-Phenyl-2-triethylsilyl-4-furanmethanol

HRID 326371

反应方程式

HRID 326371 反应方程式
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]1([C:13]2[C:17]([CH:18]=[O:19])=[CH:16][O:15][C:14]=2[Si:20]([CH2:25][CH3:26])([CH2:23][CH3:24])[CH2:21][CH3:22])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>O1CCCC1>[C:7]1([C:13]2[C:17]([CH2:18][OH:19])=[CH:16][O:15][C:14]=2[Si:20]([CH2:23][CH3:24])([CH2:25][CH3:26])[CH2:21][CH3:22])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

参与物

4

反应物 2

HCID 150371493-Phenyl-2-triethylsilyl-4furaldehydeHCID 21226445Aluminium lithium hydride

产物 1

HCID 150371503-Phenyl-2-triethylsilyl-4-furanmethanol

试剂、催化剂与溶剂 1

HCID 8028四氢呋喃溶剂

实验过程

LiAlH4 (1.0M solution in hexane, 1.48 ml, 1.48 mmol) was added dropwise to a solution of 3-phenyl-2-triethylsilyl-4-furaldehyde (422 mg, 1.48 mmol) in tetrahydrofuran (10 ml) at 0 degrees under argon. This mixture was warmed to room temperature, quenched wtih ice-cold 5% (V/V) hydrochloric acid and the organics were extracted into ethyl ether. The combined fractions were washed with saturated sodium bicarbonate, H2O and brine. The dried extracts (magnesium sulfate) were concentrated to an oil which was purified by flash chromatography on silica using 20% ethyl acetate/hexanes to give the title compound. IR (neat): 3300 (broad); 2953 cm-1.

后处理

  1. customquenched wtih ice-cold 5% (V/V) hydrochloric acid
  2. extractionthe organics were extracted into ethyl ether
  3. washThe combined fractions were washed with saturated sodium bicarbonate, H2O and brine
  4. concentrationThe dried extracts (magnesium sulfate) were concentrated to an oil which
  5. customwas purified by flash chromatography on silica using 20% ethyl acetate/hexanes

来源与证据

ORD记录
ord-ce500028719642558ccd41b5c1aece98
来源数据集
uspto-grants-1993_12
专利号
US05268387

关联笔记

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