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

HRID 1778351
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1778351
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[C:11]1([S:17]([CH2:20][C:21]2[C:26]([C:27]([O:29][CH3:30])=[O:28])=[C:25]([OH:31])[C:24]([C:32]3[CH:36]=[CH:35][O:34][C:33]=3[CH:37]=O)=[CH:23][CH:22]=2)(=[O:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C:39](OCC)(=O)C.[Cl-].[NH4+]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[C:11]1([S:17]([CH2:20][C:21]2[C:26]([C:27]([O:29][CH3:30])=[O:28])=[C:25]([OH:31])[C:24]([C:32]3[CH:36]=[CH:35][O:34][C:33]=3[CH:37]=[CH2:39])=[CH:23][CH:22]=2)(=[O:19])=[O:18])[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 86684730Methyl 6-(benzenesulfonylmethyl)-3-(2-formylfuran-3-yl)-2-hydroxybenzoate2×

Produkt 1

HCID 66685753Methyl 6-(benzenesulfonylmethyl)-2-hydroxy-3-(2-vinylfuran-3-yl)-benzoate

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 74505Methyltriphenyliphosphonium bromideKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

A suspension of methyltriphenylphosphonium bromide (pre-dried under vacuum at 60° C., 3.80 g) in THF (60 mL) was cooled to 5° C., under nitrogen. Potassium bis-(trimethylsilyl)amide (0.5M in toluene, 21.3 mL) was added and the suspension was warmed to room temperature and stirred for 45 minutes. It was cooled to −78° C. and a solution of methyl 6-(benzenesulfonylmethyl)-3-(2-formylfuran-3-yl)-2-hydroxybenzoate (Intermediate 28, 1.42 g) in THF (40 mL) was added and the mixture was warmed to room temperature and stirred for 2.5 hours. Ethyl acetate and a saturated aqueous solution of ammonium chloride were added to the mixture 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 15-35% to give methyl 6-(benzenesulfonylmethyl)-2-hydroxy-3-(2-vinylfuran-3-yl)-benzoate (1.24 g) as a white solid.

Aufarbeitung

  1. temperaturethe suspension was warmed to room temperature
  2. temperatureIt was cooled to −78° C.
  3. temperaturethe mixture was warmed to room temperature
  4. stirringstirred for 2.5 hours
  5. customthe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customThe filtrate was evaporated to dryness
  10. customthe residue was purified by chromatography on silica
  11. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 15-35%

Quellen und Nachweise

ORD-Eintrag
ord-b6507285499f4280a0aa9ff34b0cf0e3
Quelldatensatz
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09266896B2

Notizen zur Reaktion

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