Potassium tert-butoxide → HCID 178437588, Verbindung

HRID 928114Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 928114
[CH3:1]C(C)([O-])C.[K+].[Br:7][C:8]1[S:12][C:11]([C:13]([C@H:15]2[CH2:20][CH2:19][C@H:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:17][CH2:16]2)=O)=[N:10][CH:9]=1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(OCC)C.O.C(OCC)(=O)C>[Br:7][C:8]1[S:12][C:11]([C:13]([C@H:15]2[CH2:20][CH2:19][C@H:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:17][CH2:16]2)=[CH2:1])=[N:10][CH:9]=1

Komponenten

7

Edukt 2

HCID 23665647Potassium tert-butoxideHCID 178472369HCID 178472369, Verbindung

Produkt 1

HCID 178437588HCID 178437588, VerbindungAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 74505Methyltriphenyliphosphonium bromideKatalysatorHCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Methyl(triphenyl)phosphonium bromide (774 mg, 2.166 mmol) was suspended in anhydrous diethyl ether (5 mL) and potassium tert-butoxide (2.311 mmol, 1.78 M in THF, 1.29 mL) was added at 0° C. dropwise. The suspension was left 25 min at the same temperature (solution became orange-brown). A solution of diethyl ether (1 ml) and ethyl trans-4-[(5-bromo-1,3-thiazol-2-yl)carbonyl]cyclohexanecarboxylate (500 mg, 1.444 mmol) was added dropwise at 0° C. The mixture was left at the same temperature for 30 min, allowed to reach room temperature, left under stirring additional 90 min, diluted with water and taken up in ethyl acetate. The organic phase was washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel (0% to 10% EtOAc in hexanes) to afford ethyl trans-4-[1-(5-bromo-1,3-thiazol-2-yl)ethenyl]-cyclohexanecarboxylate (62%) as an oil. MS ESI calc'd. for C14H18BrNO2S for [M+H]+ 344, 346. found 344, 346. 1H NMR (500 MHz, CDCl3) δ 7.55 (s, 1H), 5.60 (s, 1H), 5.19 (s, 1H), 4.04 (q, J=7.0, 2H), 2.62-2.78 (m, 1H), 2.20-2.30 (m, 1H), 1.90-2.02 (m, 3H), 1.50-1.60 (m, 2H), 1.10-1.30 (m, 2H), 1.17 (t, J=7.0, 3H), 0.72-0.82 (m, 1H).

Aufarbeitung

  1. waitThe mixture was left at the same temperature for 30 min
  2. customto reach room temperature
  3. waitleft
  4. washThe organic phase was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by chromatography on silica gel (0% to 10% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-70bf2a6067464dacbdf21e4e0ad166ce
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09290490B2

Notizen zur Reaktion

Wird geladen…