Potassium periodate → (R)-4-Benzyloxy-3-methylbutanal

HRID 466267

반응식

HRID 466267 반응식
[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

참가 물질

6

반응물 2

HCID 516896Potassium periodateHCID 14608667{[(2-Methylpent-4-EN-1-YL)oxy]methyl}benzene

생성물 1

HCID 11116875(R)-4-Benzyloxy-3-methylbutanal수율 81%

시약·촉매·용매 3

HCID 30318Osmium Tetroxide촉매HCID 180Acetone용매HCID 962Water용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-32bef3fdc944401e9dfafddf455ae440
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05155228

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