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

HRID 2177809
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2177809
[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
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962
Water
Lösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

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.

Aufarbeitung

  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%

Quellen und Nachweise

ORD-Eintrag
ord-b40b7a33196244568886525d95e0d6e1
Quelldatensatz
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09067905B2

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