Ethyl Acetate → Methyl 6-(benzenesulfonylmethyl)-2-hydroxy-3-(2-hydroxymethylfuran-3-yl)-benzoate

HRID 1778347Notes

Reaction equation

HRID 1778347 reaction equation
[BH4-].[Na+].[C:3]1([S:9]([CH2:12][C:13]2[C:18]([C:19]([O:21][CH3:22])=[O:20])=[C:17]([OH:23])[C:16]([C:24]3[CH:28]=[CH:27][O:26][C:25]=3[CH:29]=[O:30])=[CH:15][CH:14]=2)(=[O:11])=[O:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl-].[NH4+].C(OCC)(=O)C>CO.C1COCC1.O>[C:3]1([S:9]([CH2:12][C:13]2[C:18]([C:19]([O:21][CH3:22])=[O:20])=[C:17]([OH:23])[C:16]([C:24]3[CH:28]=[CH:27][O:26][C:25]=3[CH2:29][OH:30])=[CH:15][CH:14]=2)(=[O:11])=[O:10])[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 86684730Methyl 6-(benzenesulfonylmethyl)-3-(2-formylfuran-3-yl)-2-hydroxybenzoate2×

Product 1

HCID 66685310Methyl 6-(benzenesulfonylmethyl)-2-hydroxy-3-(2-hydroxymethylfuran-3-yl)-benzoateYield 96.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium borohydride (0.031 g) was added to a solution of methyl 6-(benzenesulfonylmethyl)-3-(2-formylfuran-3-yl)-2-hydroxybenzoate (Intermediate 28, 0.67 g) in methanol (6 mL) and THF (12 mL) at 0° C. and the resultant mixture was stirred at 0° C. for 10 minutes. Saturated aqueous ammonium chloride, ethyl acetate and water were added and the organic layer was separated, washed with 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 30-80% to give methyl 6-(benzenesulfonylmethyl)-2-hydroxy-3-(2-hydroxymethylfuran-3-yl)-benzoate (0.65 g) as a white solid.

Workup

  1. customthe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness
  6. customthe residue was purified by chromatography on silica
  7. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 30-80%

Sources & evidence

ORD record
ord-6d76f35165aa45299da928e0c9c3b842
Source dataset
uspto-grants-2016_02
Patent number
US09266896B2

Reaction notes

Loading…