Sulfuric Acid → t-Butyl 3-(furan-3-yl)-2-methoxy-6-(phenylthiomethyl)benzoate

HRID 2177862Notes

Reaction equation

HRID 2177862 reaction equation
S(=O)(=O)(O)O.S([O-])([O-])(=O)=O.[Mg+2].[O:12]1[CH:16]=[CH:15][C:14]([C:17]2[C:18]([O:34][CH3:35])=[C:19]([C:23]([CH2:26][S:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:24][CH:25]=2)[C:20]([OH:22])=[O:21])=[CH:13]1.C(=O)([O-])O.[Na+]>C(Cl)Cl.C(O)(C)(C)C>[O:12]1[CH:16]=[CH:15][C:14]([C:17]2[C:18]([O:34][CH3:35])=[C:19]([C:23]([CH2:26][S:27][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[CH:24][CH:25]=2)[C:20]([O:22][C:14]([CH3:17])([CH3:15])[CH3:13])=[O:21])=[CH:13]1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 24083Sulfuric acid magnesium salt (1:1)HCID 516892Sodium BicarbonateHCID 671080273-(Furan-3-yl)-2-methoxy-6-(phenylthiomethyl)benzoic acid2×

Product 1

HCID 67107958t-Butyl 3-(furan-3-yl)-2-methoxy-6-(phenylthiomethyl)benzoateYield 119.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 6386tert-ButanolSolvent

Procedure

Concentrated sulphuric acid (0.31 g) was added to a stirred suspension of magnesium sulphate (1.31 g) in DCM (10 ml) in a sealed vial and the mixture was stirred for 5 minutes before addition of a solution of 3-(furan-3-yl)-2-methoxy-6-(phenylthiomethyl)benzoic acid (Intermediate 223, 0.96 g) in DCM (8 ml) and t-butanol (1.03 g). The mixture was stirred in a sealed tube for 48 hours. DCM and saturated aqueous sodium hydrogen carbonate were added to the mixture and the organic layer was separated, 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 0-100%, to give t-butyl 3-(furan-3-yl)-2-methoxy-6-(phenylthiomethyl)benzoate (0.67 g) as a colourless gum.

Workup

  1. customthe organic layer was separated
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customThe filtrate was evaporated to dryness
  5. customthe residue was purified by chromatography on silica
  6. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-100%

Sources & evidence

ORD record
ord-e5858a4945d94139aa33aae9a02e484e
Source dataset
uspto-grants-2015_06
Patent number
US09067905B2

Reaction notes

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