Hydrogen Peroxide → HCID 57757240, compound

HRID 227894Notes

Reaction equation

HRID 227894 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:14])[CH2:9][CH2:10][CH2:11][CH:12]=[CH2:13])=[CH:4][CH:3]=1.B(F)(F)F.CC[O:21]CC.[OH-].[Na+].OO.C([O-])([O-])=O.[K+].[K+]>[BH4-].[Na+].COCCOCCOC.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([OH:14])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:21])=[CH:6][CH:7]=1

Participants

9

Reactant 5

HCID 784Hydrogen PeroxideHCID 8000Boron trifluoride etherateHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 57757252HCID 57757252, compound

Product 1

HCID 57757240HCID 57757240, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8150DiglymeSolvent2×HCID 4311764Sodium borohydrideSolvent

Procedure

1-(4-Bromo-phenyl)-hex-5-en-1-ol (1 g) was dissolved in 0.5 M NaBH4 in diglyme (9 mL) and chilled in an ice bath. BF3.OEt2 (1 mL) in diglyme (4 mL) was added with vigorous stirring. Stirring was continued for 1 hour and water (1 mL) was added. 3M NaOH (2 mL) was added followed by 30% H2O2 (3 mL). Anhydrous K2CO3 (5 g) was added and the solvent was decanted. The K2CO3 was washed with ethyl acetate and the combined organics were dried (Na2SO4) and evaporated. Distillation under vacuum removed most of the remaining diglyme. The residue was purified by column chromatography (light petroleum:diethyl ether 2:1) to give a clear oil which solidified to give the title compound as a white powder. 13C NMR (CDCl3): δ 25.4, 25.6, 32.5, 39.0, 62.7, 73.8, 121.2, 127.7, 131.5 and 143.9. 1H NMR (CDCl3): δ 1.40 (4H, m), 1.52 (2H, m), 1.74 (2H, m), 3.61 (2H, t, J=6.5 Hz), 4.74 (1H, t, J=6.5 Hz), 7.20 (2H, d, J=8.2 Hz) and 7.41 (2H, d, J=8.2 Hz).

Workup

  1. temperaturechilled in an ice bath
  2. customthe solvent was decanted
  3. washThe K2CO3 was washed with ethyl acetate
  4. dry with materialthe combined organics were dried (Na2SO4)
  5. customevaporated
  6. distillationDistillation under vacuum
  7. customremoved most of the remaining diglyme
  8. customThe residue was purified by column chromatography (light petroleum:diethyl ether 2:1)
  9. customto give a clear oil which

Sources & evidence

ORD record
ord-48eeec696ead4e2cb48abee8c6e60424
Source dataset
uspto-grants-2009_07
Patent number
US07560597B2

Reaction notes

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