Hydrogen Peroxide → Biphenyl-4-sulfonic acid-(4-hydroxybutyl)-(5-hydroxypentyl)-amide

HRID 2425123Notes

Reaction equation

HRID 2425123 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]([CH:22]=[CH:23][CH2:24][CH2:25][CH3:26])[S:7]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)(=[O:9])=[O:8].B(F)(F)F.[OH-].[Na+].OO.C([O-])([O-])=[O:36].[K+].[K+]>[BH4-].[Na+].COCCOCCOC.O.O(CC)CC>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][OH:36])[S:7]([C:10]1[CH:11]=[CH:12][C:13]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:14][CH:15]=1)(=[O:9])=[O:8]

Participants

10

Reactant 5

HCID 784Hydrogen PeroxideHCID 6356Boron trifluorideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 67245842Biphenyl-4-sulfonic acid-(4-hydroxybutyl)-penten-1-yl-amide

Product 1

HCID 11703837Biphenyl-4-sulfonic acid-(4-hydroxybutyl)-(5-hydroxypentyl)-amide

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8150DiglymeSolvent2×HCID 4311764Sodium borohydrideSolvent

Procedure

Biphenyl-4-sulfonic acid-(4-hydroxybutyl)-penten-1-yl-amide (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 decanted. The K2CO3 was washed with ethyl acetate and the combined organics dried (Na2SO4) and evaporated. Distillation under vacuum removed most of the remaining diglyme. The residue was purified by column chromatography (ethyl acetate/petrol) to give the title compound as a white powder. δC (DMSO, 62.9 MHz): 22.7, 25.2, 28.3, 29.6, 32.1, 48.0, 60.3, 60.5, 127.1, 127.2, 127.6, 128.6, 129.2, 138.1, 138.4 and 144.1.

Workup

  1. temperaturechilled in an ice bath
  2. customthe solvent decanted
  3. washThe K2CO3 was washed with ethyl acetate
  4. dry with materialthe combined organics dried (Na2SO4)
  5. customevaporated
  6. distillationDistillation under vacuum
  7. customremoved most of the remaining diglyme
  8. customThe residue was purified by column chromatography (ethyl acetate/petrol)

Sources & evidence

ORD record
ord-c21464a057a84d7ea8b315cf601312c9
Source dataset
uspto-grants-2011_06
Patent number
US07964643B2

Reaction notes

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