Hydrogen Peroxide → Methyl 6-(benzenesulfonylmethyl)-2-hydroxy-3-[2-(2-hydroxyethyl)-furan-3-yl]-benzoate

HRID 1778350Notes

Reaction equation

HRID 1778350 reaction equation
[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15]([OH:21])[C:14]([C:22]3[CH:26]=[CH:25][O:24][C:23]=3[CH:27]=[CH2:28])=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.OO.O.C(OCC)(=[O:34])C>C1COCC1>[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15]([OH:21])[C:14]([C:22]3[CH:26]=[CH:25][O:24][C:23]=3[CH2:27][CH2:28][OH:34])=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 8857Ethyl AcetateHCID 66685753Methyl 6-(benzenesulfonylmethyl)-2-hydroxy-3-(2-vinylfuran-3-yl)-benzoate2×

Product 1

HCID 66685569Methyl 6-(benzenesulfonylmethyl)-2-hydroxy-3-[2-(2-hydroxyethyl)-furan-3-yl]-benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

A solution of 9-borobicyclononane (0.5M in THF, 12.6 mL) was added to methyl 6-(benzenesulfonylmethyl)-2-hydroxy-3-(2-vinylfuran-3-yl)-benzoate (Intermediate 24, 1.0 g) in THF (20 mL) at 50° C. and the resultant mixture was stirred and heated at 50° C. for 75 minutes. After cooling to room temperature, 35% hydrogen peroxide (2 mL) was added and the mixture was stirred for 1.5 hours. Water and ethyl acetate were added to the mixture and the organic layer was separated, washed with water, sodium metabisulfite and brine, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 30-70%. The product was triturated with diethyl ether and the solid was collected by filtration and dried in vacuo to give methyl 6-(benzenesulfonylmethyl)-2-hydroxy-3-[2-(2-hydroxyethyl)-furan-3-yl]-benzoate (0.4 g).

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe organic layer was separated
  3. washwashed with water, sodium metabisulfite and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness
  7. customthe residue was purified by chromatography on silica
  8. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 30-70%
  9. customThe product was triturated with diethyl ether
  10. filtrationthe solid was collected by filtration
  11. customdried in vacuo

Sources & evidence

ORD record
ord-417935d7e059470cb9ba095b3439a3f6
Source dataset
uspto-grants-2016_02
Patent number
US09266896B2

Reaction notes

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