Water → 2,3-Dihydro[1,4]dioxino[2,3-f]quinolin-2-ylmethyl4-methylbenzenesulfonate

HRID 720374Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 720374
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][C@@H:13]2[O:18][C:17]3[C:19]([CH:26]=[CH:27][CH:28]=O)=[C:20]([N+:23]([O-])=O)[CH:21]=[CH:22][C:16]=3[O:15][CH2:14]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.O>C(O)(=O)C.C(O)C.[Fe]>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][CH:13]2[O:18][C:17]3=[C:19]4[C:20](=[CH:21][CH:22]=[C:16]3[O:15][CH2:14]2)[N:23]=[CH:28][CH:27]=[CH:26]4)(=[O:9])=[O:10])=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 962WaterHCID 86586348{(2R)-7-nitro-8-[3-oxo-1-propenyl]-2,3-dihydro-1,4-benzodioxin-2-yl}methyl4-methylbenzenesulfonate

Produkt 1

HCID 218920582,3-Dihydro[1,4]dioxino[2,3-f]quinolin-2-ylmethyl4-methylbenzenesulfonate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 18476134Acetic acid ethanolLösungsmittel

Versuchsvorschrift

To a solution of {(2R)-7-nitro-8-[3-oxo-1-propenyl]-2,3-dihydro-1,4-benzodioxin-2-yl}methyl 4-methylbenzenesulfonate (3.50 g, 8.35 mmole) in 200 mL of acetic acid/ethanol (1:1) was added 2.35 g (42.1 mmole) of iron powder and the mixture was heated at reflux under nitrogen for 8 hours. After the reaction was complete, 150 mL of water was added and the mixture filtered through a pad of celite. The filtrate was neutralized with saturated sodium bicarbonate and extracted with ethyl acetate. The extract was dried over magnesium sulfate, filtered, and evaporated in vacuum. The residue was column chromatographed on silica gel using a gradient elution commencing with 20% ethyl acetate/hexane and ending with 70% ethyl acetate/hexane to give 1.85 g of the (R)-enantiomer of the title compound as a yellow oil. 1H-NMR (CDCl3): doublet 8.8 δ (1 H); doublet 8.2 δ (1 H); doublet 7.8 δ (2 H); doublet 7.6 δ (1 H); multiplet 7.35 δ (1 H); multiplet 7.25 δ (3 H); multiplet 4.6 δ (1 H); multiplet 4.3–4.4 δ (3 H); multiplet 4.2 δ (1 H); singlet 2.4 δ (3 H).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureat reflux under nitrogen for 8 hours
  3. filtrationthe mixture filtered through a pad of celite
  4. extractionextracted with ethyl acetate
  5. dry with materialThe extract was dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuum
  8. customchromatographed on silica gel using a gradient elution commencing with 20% ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-79b1aa1e6cc648778af0e91e39ef5243
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07135479B2

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