Water → N-(5-Bromo-4'-methoxy-3H-spiro[benzofuran-2,1'-cyclohexane]-3-ylidene)-2-methylpropane-2-sulfinamide

HRID 1770957

Reaktionsgleichung

Reaktionsgleichung von HRID 1770957
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([C:8]([C:10]2([OH:18])[CH2:15][CH2:14][CH:13]([O:16][CH3:17])[CH2:12][CH2:11]2)=O)[CH:7]=1.[CH3:20][C:21]([S:24]([NH2:26])=[O:25])([CH3:23])[CH3:22].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:3]=[CH:4][C:5]2[O:18][C:10]3([CH2:15][CH2:14][CH:13]([O:16][CH3:17])[CH2:12][CH2:11]3)[C:8](=[N:26][S:24]([C:21]([CH3:23])([CH3:22])[CH3:20])=[O:25])[C:6]=2[CH:7]=1

Komponenten

7

Edukt 3

HCID 962WaterHCID 3382465Tert-ButanesulfinamideHCID 67979505(5-Bromo-2-fluorophenyl)(1-hydroxy-4-methoxycyclohexyl)methanone2×

Produkt 1

HCID 67979520N-(5-Bromo-4'-methoxy-3H-spiro[benzofuran-2,1'-cyclohexane]-3-ylidene)-2-methylpropane-2-sulfinamideAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 76524Titanium tetraethoxideKatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 178479889HCID 178479889, VerbindungLösungsmittel

Versuchsvorschrift

To a mixture of 5-bromo-4′-methoxy-3H-spiro[benzofuran-2,1′-cyclohexan]-3-one (Intermediate 12, 2.8 g, 9.00 mmol) and 2-methylpropane-2-sulfinamide (2.024 g, 16.20 mmol) in methyl THF (15 mL) was added titanium ethoxide (3.71 mL, 18.00 mmol) and the reaction was heated to reflux. After 21 h the reaction was allowed to cool to r.t. whereafter it was diluted with EtOAc (150 mL). Water (12 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. The crude product was purified by flash chromatography using a gradient of 0%-50% EtOAc in heptane, yielding 2.41 g of the title compound (65% yield): 1H NMR (500 MHz, CDCl3) δ ppm 1.33 (s, 9H), 1.81 (m, 6H), 2.12 (d, 2H), 3.33 (m, 1H), 3.42 (s, 3H), 6.94 (d, 1H), 7.59 (dd, 1H), 8.53 (m, 1H); MS (ES+) m/z 415 [M+H]+.

Aufarbeitung

  1. temperaturethe reaction was heated to reflux
  2. waitthe mixture was left
  3. stirringwithout stirring for 1.5 h
  4. filtrationThe solids were filtered off
  5. customthe organics were evaporated
  6. customThe crude product was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-26e04c2f4e9c4bed96bb115e9ad4d569
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09248129B2

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