Tetrahydrofuran → Methyl 6-(benzenesulphonylmethyl)-2-ethyl-3-(furan-3-yl)benzoate

HRID 2177809Notes

Reaction equation

HRID 2177809 reaction equation
[O-]P([O-])([O-])=O.[K+].[K+].[K+].[C:9]1([S:15]([CH2:18][C:19]2[C:24]([C:25]([O:27][CH3:28])=[O:26])=[C:23](OS(C(F)(F)F)(=O)=O)[C:22]([C:37]3[CH:41]=[CH:40][O:39][CH:38]=3)=[CH:21][CH:20]=2)(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH2:42]1COC[CH2:43]1>O>[C:9]1([S:15]([CH2:18][C:19]2[C:24]([C:25]([O:27][CH3:28])=[O:26])=[C:23]([CH2:42][CH3:43])[C:22]([C:37]3[CH:41]=[CH:40][O:39][CH:38]=3)=[CH:21][CH:20]=2)(=[O:16])=[O:17])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 62657Potassium Phosphate, TribasicHCID 86677115Methyl 6-(benzenesulphonylmethyl)-3-(furan-3-yl)-2-(trifluoromethanesulphonyloxy)benzoate2×

Product 1

HCID 67108200Methyl 6-(benzenesulphonylmethyl)-2-ethyl-3-(furan-3-yl)benzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of potassium phosphate tribasic (0.244 g), methyl 6-(benzenesulphonylmethyl)-3-(furan-3-yl)-2-(trifluoromethanesulphonyloxy)benzoate (Intermediate 123, 0.2 g) in THF (2 ml) and water (1 ml) was sealed in a microwave vial and degassed with argon. Palladium (II) chloride dppf complexed with DCM (0.02 g) and triethylborane (0.29 ml) were added and the mixture was heated in the microwave at 140° C. for 15 minutes. After cooling, ethyl acetate and water were added and the organic layer was separated, washed with brine, dried (MgSO4) 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 10-18% to give methyl 6-(benzenesulphonylmethyl)-2-ethyl-3-(furan-3-yl)benzoate (0.092 g) as a white solid.

Workup

  1. customwas sealed in a microwave vial
  2. customdegassed with argon
  3. additionwere added
  4. temperatureAfter cooling
  5. additionethyl acetate and water were added
  6. customthe organic layer was separated
  7. washwashed with brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customThe filtrate was evaporated to dryness
  11. customthe residue was purified by chromatography on silica eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 10-18%

Sources & evidence

ORD record
ord-b40b7a33196244568886525d95e0d6e1
Source dataset
uspto-grants-2015_06
Patent number
US09067905B2

Reaction notes

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