Water → HCID 19386922, Verbindung

HRID 1655381Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1655381
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][C:11]([CH3:14])([CH3:13])[C:10]([CH2:15][NH:16][C:17](=[O:22])[C:18]([F:21])([F:20])[F:19])=[CH:9][C:8]=2[CH:23]=1)([O-:3])=[O:2].ClC1C=CC=C(C(OO)=[O:32])C=1.O.C(=O)([O-])O.[Na+]>ClCCl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][C:11]([CH3:13])([CH3:14])[C:10]3([CH2:15][NH:16][C:17](=[O:22])[C:18]([F:21])([F:19])[F:20])[O:32][CH:9]3[C:8]=2[CH:23]=1)([O-:3])=[O:2]

Komponenten

6

Edukt 4

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 193871406-nitro-2,2-dimethyl-3-(trifluoroacetamido)methyl-2H-1-benzopyran

Produkt 1

HCID 19386922HCID 19386922, VerbindungAusbeute 81,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 6-nitro-2,2-dimethyl-3-(trifluoroacetamido)methyl-2H-1-benzopyran (0.5 g, 1.52 mmol) in dichloromethane (10 ml) at 0° C. was treated with m-chloroperbenzoic acid (70%, 0.45 g, 1.52 mmol). After stirring for sixteen hours at room temperature, water and sodium hydrogen carbonate were added and the organic phase separated and evaporated under reduced pressure. The residue was chromatographed on silica gel, eluting with dichloromethane/acetone (95/5), to give 0.43 g of 6-nitro-2,2-dimethyl-3-(trifluoroacetamido)methyl-3,4-dihydro-3,4-epoxy-2H-1-benzopyran 1NMR (CDCl3): δ 1.4 (s, 3H) , 1.6 (s, 3H), 3.7 (dd,1H), 3.85 (s, 1H), 4.15 (dd, 1H), 6.70 (br.s, 1H), 6.95 (d, 1H), 8.2 (d, 1H), 8.30 (s, 1H).

Aufarbeitung

  1. customthe organic phase separated
  2. customevaporated under reduced pressure
  3. customThe residue was chromatographed on silica gel
  4. washeluting with dichloromethane/acetone (95/5)

Quellen und Nachweise

ORD-Eintrag
ord-8f058da0ad61490eb3ef4e3f43a0048c
Quelldatensatz
uspto-grants-1993_10
Patentnummer
US05250547

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