Hydrogen Peroxide → HCID 22797510, compound

HRID 2397621Notes

Reaction equation

HRID 2397621 reaction equation
B(F)(F)F.[CH2:5]([O:12][C@@H:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH:14]=[CH2:15])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[BH4-].[Na+].[OH-:23].[Na+].OO>O1CCCC1.O>[CH2:5]([O:12][C@@H:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:14][CH2:15][OH:23])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

8

Reactant 5

HCID 784Hydrogen PeroxideHCID 6356Boron trifluorideHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 10420947HCID 10420947, compound

Product 1

HCID 22797510HCID 22797510, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of borontrifluoride. etherate (2.1ml.; 16.7 millimole) in dry tetrahydrofuran (5 ml.) is added dropwise to a stirred mixture of 3(S)-benzyloxy-1-octene (2.19 g., 10 millimole) and sodium borohydride (0.47 g., 12.5 millimole) in dry tetrahydrofuran (25 ml.) maintained at 0° to 5° C. under a nitrogen atmosphere. The resulting reaction mixture is warmed to and maintained at room temperature for 15 hours. After cooling to 0° to 5° C., the reaction mixture is treated cautiously via successive dropwise additions with water (2 ml.), 5N sodium hydroxide (4 ml.) and 30% hydrogen peroxide (8 ml.). After stirring at room temperature for 1/2 hour, the resulting mixture is diluted with ice water and extracted with chloroform three times. The combined organic extract is washed with saturated aqueous brine, dried over magnesium sulfate, and filtered. Evaporation of the filtrate in vacuo provides the title compound as a viscous oil (2.37 g., 100%).

Workup

  1. temperaturemaintained at 0° to 5° C. under a nitrogen atmosphere
  2. customThe resulting reaction mixture
  3. temperatureis warmed to and
  4. temperatureAfter cooling to 0° to 5° C.
  5. extractionextracted with chloroform three times
  6. extractionThe combined organic extract
  7. washis washed with saturated aqueous brine
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customEvaporation of the filtrate in vacuo

Sources & evidence

ORD record
ord-085d72567fdf4730a48a814227ff5343
Source dataset
uspto-grants-1977_05
Patent number
US04022794

Reaction notes

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