过碘酸钾 → (R)-4-Benzyloxy-3-methylbutanal

HRID 466267

反应方程式

HRID 466267 反应方程式
[CH3:1][CH:2]([CH2:12][CH:13]=C)[CH2:3][O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.I([O-])(=O)(=O)=[O:16].[K+]>CC(C)=O.O.[Os](=O)(=O)(=O)=O>[CH2:5]([O:4][CH2:3][C@H:2]([CH3:1])[CH2:12][CH:13]=[O:16])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

参与物

6

反应物 2

HCID 516896过碘酸钾HCID 14608667{[(2-Methylpent-4-EN-1-YL)oxy]methyl}benzene

产物 1

HCID 11116875(R)-4-Benzyloxy-3-methylbutanal收率 81%

试剂、催化剂与溶剂 3

HCID 30318锇酸催化剂HCID 180丙酮溶剂HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂

实验过程

A 250 mL round-bottomed flask, equipped with a magnetic stirring bar and a thermometer was fitted with a septum and a nitrogen inlet. The apparatus was charged with benzyl 2-methyl-4-penten-1-yl ether (2.39 g, 12.5 mmol) in 75 mL of acetone and 25 mL of water. Osmium tetroxide (0.833 mL of an 0.15M aqueous solution, 0.125 mmol) was added in one portion, followed by potassium periodate (6.04 g, 26.2 mmol) in three equal portions. The resulting slurry was stirred for 6 hours at room temperature and decanted into a 500 mL separatory funnel. The aqueous layer was extracted with 3×200 mL of diethyl ether. Each washing was stirred over the solids for 5 minutes, washed with 150 mL of saturated aqueous sodium thiosulfate and 100 mL of saturated aqueous sodium chloride. The combined organic layers were dried over sodium sulfate, filtered, concentrated and chromatographed (4×20 cm column; 4:1 hexane:ethyl acetate) to afford 1.94 g (81%) of aldehyde 4 as a colorless oil. Rf =0.37 (4:1 hexane:ethyl acetate).

后处理

  1. customA 250 mL round-bottomed flask, equipped with a magnetic stirring bar
  2. customa thermometer was fitted with a septum and a nitrogen inlet
  3. customdecanted into a 500 mL separatory funnel
  4. extractionThe aqueous layer was extracted with 3×200 mL of diethyl ether
  5. stirringEach washing was stirred over the solids for 5 minutes
  6. washwashed with 150 mL of saturated aqueous sodium thiosulfate and 100 mL of saturated aqueous sodium chloride
  7. dry with materialThe combined organic layers were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customchromatographed (4×20 cm column; 4:1 hexane:ethyl acetate)

来源与证据

ORD记录
ord-32bef3fdc944401e9dfafddf455ae440
来源数据集
uspto-grants-1992_10
专利号
US05155228

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