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Chlorotrimethylsilane → HCID 71520077, Verbindung

HRID 633663
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 633663
C1COCC1.[CH3:6][O:7][C:8]1[C@:15]2([CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])[C:16](=[O:17])[C@@H:11]([C@:12]([CH3:42])([CH2:28][CH2:29][CH2:30][C:31]([CH3:41])([O:33][Si:34]([CH2:39][CH3:40])([CH2:37][CH3:38])[CH2:35][CH3:36])[CH3:32])[C@@H:13]([CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26])[CH2:14]2)[C:10](=[O:43])[CH:9]=1.Cl[Si:45]([CH3:48])([CH3:47])[CH3:46].[Li]N1C(C)(C)CCCC1(C)C>CCOC(C)=O.CCCCCC>[CH3:6][O:7][C:8]1[C@:15]2([CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])[C:16](=[O:17])[C@@H:11]([C@:12]([CH3:42])([CH2:28][CH2:29][CH2:30][C:31]([CH3:41])([O:33][Si:34]([CH2:37][CH3:38])([CH2:35][CH3:36])[CH2:39][CH3:40])[CH3:32])[C@@H:13]([CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26])[CH2:14]2)[C:10](=[O:43])[C:9]=1[Si:45]([CH3:48])([CH3:47])[CH3:46]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 6397ChlorotrimethylsilaneHCID 8028Tetrahydrofuran2×HCID 71499447HCID 71499447, VerbindungHCID 178418821HCID 178418821, Verbindung

Produkt 1

HCID 71520077HCID 71520077, VerbindungAusbeute 90,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8058
Hexane
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A THF (1 mL) solution of 44 (22.9 mg, 42.0 μmol, 1 equiv.) was cooled to −78° C. in a 10-mL test tube, and chlorotrimethylsilane (53 μL, 0.42 mmol, 10 equiv.) and a freshly prepared THF solution of lithium tetramethylpiperidide (0.50 M, 420 μL, 0.21 mmol, 5 equiv.) were sequentially added. The golden yellow solution was slowly warmed to 0° C. over 1 h and quenched at 0° C. with saturated aqueous NaHCO3. The mixture was warmed to room temperature and extracted thrice with EtOAc. The organic extracts were combined, washed with H2O and brine, dried over Na2SO4, filtered, and concentrated in vacuo to a yellow oil. Flash column chromatography (20 mL SiO2, 98:2 hexane:EtOAc) afforded 23.4 mg (37.9 μmol, 90% yield) of 45 as a colorless oil. TLC Rf 0.40 (95:5 hexane:EtOAc). 1H NMR (600 MHz; CDCl3): δ 5.02-4.97 (m, 2H), 3.83 (s, 3H), 3.11 (s, 1H), 2.51 (dd, J=14.4, 6.3 Hz, 1H), 2.37 (dd, J=14.5, 7.5 Hz, 1H), 2.15-2.11 (m, 1H), 1.99 (dd, J=14.0, 3.7 Hz, 1H), 1.69 (s, 3H), 1.68-1.63 (m, 9H), 1.57 (s, 3H), 1.48 (td, J=12.7, 3.9 Hz, 1H), 1.46-1.37 (m, 2H), 1.30 (td, J=12.2, 4.1 Hz, 1H), 1.26-1.24 (m, 1H), 1.21 (s, 3H), 1.21 (s, 3H), 1.14 (td, J=12.6, 4.2 Hz, 1H), 0.94 (t, J=7.9 Hz, 9H), 0.80 (s, 3H), 0.57 (q, J=8.1 Hz, 6H), 0.23 (s, 9H). 13C NMR (126 MHz; CDCl3): δ 207.9, 198.6, 185.7, 133.70, 133.59, 127.7, 122.8, 120.0, 73.7, 72.6, 64.1, 59.7, 46.7, 45.7, 41.8, 39.29, 39.27, 30.6, 30.0, 29.7, 27.6, 26.02, 25.97, 18.21, 18.14, 17.88, 17.83, 7.4, 7.0, 0.8. HRMS-ESI (m/z): [M+H]+ calculated for C36H64O4Si2, 617.4416. found, 617.4395.

Aufarbeitung

  1. customquenched at 0° C. with saturated aqueous NaHCO3
  2. temperatureThe mixture was warmed to room temperature
  3. extractionextracted thrice with EtOAc
  4. washwashed with H2O and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo to a yellow oil

Quellen und Nachweise

ORD-Eintrag
ord-4e136f600d114db5a39e164def4dcd16
Quelldatensatz
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09321713B2

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