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Water → N-(5'-Bromospiro[cyclobutane-1,2'-indene]-3'(1'H)-ylidene)-2-methylpropane-2-sulfinamide

HRID 539371
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 539371
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7]3([CH2:14][CH2:13][CH2:12]3)[C:8]2=O)=[CH:4][CH:3]=1.[CH3:15][C:16]([S:19]([NH2:21])=[O:20])([CH3:18])[CH3:17].O>CN1C2C(N=C(N)NC=2NCC1CNC1C=CC(C(NC(C(O)=O)CCC(O)=O)=O)=CC=1)=O.CCOC(C)=O.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[Br:1][C:2]1[CH:10]=[C:9]2[C:5](=[CH:4][CH:3]=1)[CH2:6][C:7]1([CH2:14][CH2:13][CH2:12]1)[C:8]2=[N:21][S:19]([C:16]([CH3:18])([CH3:17])[CH3:15])=[O:20]
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Komponenten

7

Edukt 3

HCID 962WaterHCID 3382465Tert-ButanesulfinamideHCID 679796166'-Bromospiro[cyclobutane-1,2'-inden]-1'(3'H)-one2×

Produkt 1

HCID 67979440N-(5'-Bromospiro[cyclobutane-1,2'-indene]-3'(1'H)-ylidene)-2-methylpropane-2-sulfinamideAusbeute 135,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 76524
Titanium tetraethoxide
Katalysator
HCID 8857Ethyl AcetateLösungsmittel
HCID 178479889HCID 178479889, VerbindungLösungsmittel

Versuchsvorschrift

6′-Bromospiro[cyclobutane-1,2′-inden]-1′(3′H)-one (Intermediate 38, 1.1 g, 4.38 mmol), 2-methylpropane-2-sulfinamide (0.96 g, 7.88 mmol), and titanium ethoxide (1.805 mL, 8.76 mmol) were dissolved in methyl THF (20 mL), and heated to reflux overnight. The reaction was allowed to cool to r.t., then it was diluted with EtOAc (150 mL). Water (22 mL) was added dropwise over 10 min under vigorous stirring and then the mixture was left standing without stirring for 1.5 h. The solids were filtered off and the organics were evaporated to give a crude product which was purified by flash chromatography (eluent: heptane/ethylacetate 8:1) to afford the title compound (2.1 g, 77% yield), used as such in the next step: MS (ES+) m/z 354 [M+H]+.

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux overnight
  3. waitthe mixture was left
  4. stirringwithout stirring for 1.5 h
  5. filtrationThe solids were filtered off
  6. customthe organics were evaporated
  7. customto give a crude product which
  8. customwas purified by flash chromatography (eluent: heptane/ethylacetate 8:1)

Quellen und Nachweise

ORD-Eintrag
ord-4acf26295b574b43983760287b6743fe
Quelldatensatz
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08865911B2

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