(Trifluoromethyl)trimethylsilane → HCID 178472372, Verbindung

HRID 928120Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 928120
[Br:1][C:2]1[S:6][C:5]([C:7]([C@H:9]2[CH2:14][CH2:13][C@H:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][CH2:10]2)=[O:8])=[N:4][CH:3]=1.[F:20][C:21]([Si](C)(C)C)([F:23])[F:22].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.O>[Br:1][C:2]1[S:6][C:5]([C:7]([C@H:9]2[CH2:10][CH2:11][C@H:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:13][CH2:14]2)([OH:8])[C:21]([F:23])([F:22])[F:20])=[N:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 178472369HCID 178472369, Verbindung

Produkt 1

HCID 178472372HCID 178472372, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of ethyl trans-4-[(5-bromo-1,3-thiazol-2-yl) carbonyl]cyclohexane-carboxylate (608 mg, 1.756 mmol) in THF (15 ml) was added trifluoromethyl trimethylsilane (0.520 ml, 3.51 mmol). Then, tetrabutylammonium fluoride (7.0 ml, 7.00 mmol) was added to the mixture slowly. After 1 h, the mixture was diluted with water and extracted with EtOAc. The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified on silica gel (0-20% EtOAc in hexane) to afford racemic ethyl trans-4-[1-(5-bromo-1,3-thiazol-2-yl)-2,2,2-trifluoro-1-hydroxyethyl]cyclohexanecarboxylate. MS ESI calc'd. for C14H17BrF3NO3S [M+H]+ 416, 418. found 416, 418. 1H NMR (500 MHz, CDCl3) δ 7.68 (s, 1H), 4.11 (q, J=7.1, 2H), 2.47-2.32 (m, 1H), 2.28-1.92 (m, 4H), 1.55-1.16 (m, 5H), 0.90 (t, J=7.3, 3H).

Aufarbeitung

  1. extractionextracted with EtOAc
  2. washThe organic phase was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified on silica gel (0-20% EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-df3b4895c60d49f9bcb07da2fc05a112
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09290490B2

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