Fluoroacetone → Fluoro-2-methyl-4-triethylsilyl-but-3-yn-2-ol
Reaktionsgleichung
[CH2:1]([Si:3]([CH2:8][CH3:9])([CH2:6][CH3:7])[C:4]#[CH:5])[CH3:2].[Li]CCCC.[F:15][CH2:16][C:17](=[O:19])[CH3:18]>C1COCC1>[F:15][CH2:16][C:17]([CH3:18])([OH:19])[C:5]#[C:4][Si:3]([CH2:8][CH3:9])([CH2:6][CH3:7])[CH2:1][CH3:2]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -78 °C
Versuchsvorschrift
This compound was prepared according to a procedure similar to that described in Procedure B. A stirred solution of triethyl(ethynyl)silane (1.05 eq, 5.4 mL) in THF. at −78° C. was treated with n-BuLi (2.5 mol/L in hexanes, 1.1 eq) dropwise. The reaction was stirred for 15 minutes before addition of 1-fluoropropan-2-one (2.1 mL) then stirred for another hour at −78° C. whereupon it was slowly warmed to room temperature. The reaction was quenched with a saturated ammonium chloride solution then extracted with ethyl acetate. The organic layer was dried with magnesium sulfate, filtered and concentrated to give a clear oil. This crude intermediate was purified by ISCO with ELSD option (0-100% Heptane: Ethyl acetate over 25 minutes) to afford 1-fluoro-2-methyl-4-triethylsilyl-but-3-yn-2-ol. 1H NMR (400 MHz, MeOD) δ 4.81 (s, 1H), 4.36-4.27 (m, 1H), 4.24-4.14 (m, 1H), 1.45 (d, J=1.8 Hz, 3H), 1.06-0.97 (m, 9H), 0.65-0.55 (m, 6H).
Aufarbeitung
- customThis compound was prepared
- temperaturewas slowly warmed to room temperature
- customThe reaction was quenched with a saturated ammonium chloride solution
- extractionthen extracted with ethyl acetate
- dry with materialThe organic layer was dried with magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
- customto give a clear oil
- customThis crude intermediate was purified by ISCO with ELSD option (0-100% Heptane: Ethyl acetate over 25 minutes)
Quellen und Nachweise
- ORD-Eintrag
- ord-757e2507daa24ec7a5cdfc3a2801ab40
- Quelldatensatz
- uspto-grants-2015_05
- Patentnummer
- US09034866B2
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