Potassium Hydroxide → HCID 14515746, compound

HRID 1165897Notes

Reaction equation

HRID 1165897 reaction equation
[C:1]([C:4]1[C:13]2[C:7]([CH:8]=[CH:9][CH:10]=[C:11]([CH:14]([CH3:16])[CH3:15])[CH:12]=2)=[CH:6][CH:5]=1)(=O)[CH3:2].[BH4-].[Na+].[OH-].[K+]>COCCOCCOC.CCOCC.B(F)(F)F>[CH2:1]([C:4]1[C:13]2[C:7]([CH:8]=[CH:9][CH:10]=[C:11]([CH:14]([CH3:15])[CH3:16])[CH:12]=2)=[CH:6][CH:5]=1)[CH3:2]

Participants

7

Reactant 3

HCID 14797Potassium HydroxideHCID 4311764Sodium borohydrideHCID 14515745HCID 14515745, compound

Product 1

HCID 14515746HCID 14515746, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6356Boron trifluorideSolventHCID 8150DiglymeSolvent2×

Procedure

The compound (20) (1.95 g) was dissolved in a mixture of diglyme (120 ml) and ether (120 ml), and BF3 etherate (2.1 ml) was added to the mixture while stirring and cooling with ice. To thus produced solution, while stirring and cooling with ice, a diglyme (8 ml) solution of NaBH4 (700 mg) was added dropwise. After stirring for 30 minutes, the reaction solution was poured into 5% potassium hydroxide aqueous solution. The thus obtained solution was extracted with hexane, washed with water and dried. The solvent was distilled off, and the thus obtained crude product was purified by column chromatography with silica gel (200 g), eluting with hexane. The first eluted part gave the product (22) at a yield of 1.28 g (65.6%) as a blue oily substance.

Workup

  1. additionwas added to the mixture
  2. temperaturecooling with ice
  3. stirringTo thus produced solution, while stirring
  4. temperaturecooling with ice
  5. stirringAfter stirring for 30 minutes
  6. extractionThe thus obtained solution was extracted with hexane
  7. washwashed with water
  8. customdried
  9. distillationThe solvent was distilled off
  10. customthe thus obtained crude product
  11. customwas purified by column chromatography with silica gel (200 g)
  12. washeluting with hexane

Sources & evidence

ORD record
ord-387983b947454192ab5317fe6d0a59fa
Source dataset
uspto-grants-1990_03
Patent number
US04912134

Reaction notes

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