Sodium hydride → HCID 10826090, Verbindung

HRID 1776139Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1776139
C(OP([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])(COCC)=O)C.[H-].[Na+].[Si:18]([O:25][CH2:26][CH2:27][CH2:28][CH:29]=O)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]>C1COCC1>[Si:18]([O:25][CH2:26][CH2:27][CH2:28]/[CH:29]=[CH:10]/[C:11]([O:13][CH2:14][CH3:15])=[O:12])([C:21]([CH3:22])([CH3:23])[CH3:24])([CH3:19])[CH3:20]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 108889764-((Tert-butyldimethylsilyl)oxy)butanalHCID 60207715HCID 60207715, Verbindung

Produkt 1

HCID 10826090HCID 10826090, VerbindungAusbeute 48,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Ethyl 2-(ethoxy(ethoxymethyl)phosphoryl)acetate (75.8 g, 0.3386 mol) was added to NaH (13.5 g, 60%) in 600 mL THF at 0° C., and the solution was warmed at RT for 1 hour, followed by the addition of 4-(tert-butyldimethylsilyloxy)butanal (5) (57.0 g, 0.2822 mol) in THF (200 mL) at 0° C., The mixture was stirred at RT for 2 hours. After removal of the solvent, the residue was dissolved in DCM, and the mixture was washed with water (3×200 mL) and brine (3×200 mL), dried over Na2SO4 and concentrated to give the desired compound of (E)-ethyl 6-(tert-butyldimethylsilyloxy)hex-2-enoate (7) (37.0 g, yield 48%) as yellow oil which was purified by column chromatography on silica gel (eluent: PE:EA=30:1). 1H NMR (300 MHz, CDCl3): δ 0.0021 (S, 6H), 0.0857 (S, 9H), 1.197 (t, 3H), 1.600 (m, 2H), 1.197 (t, 3H), 2.240 (q, 2H), 3.586 (t, 2H), 4.098 (q, 2H), 5.832 (d, J=15.6 Hz, 1H), 6.936-6.885 (m, 1H); LC-MS found 273 (M+H)+.

Aufarbeitung

  1. customAfter removal of the solvent
  2. dissolutionthe residue was dissolved in DCM
  3. washthe mixture was washed with water (3×200 mL) and brine (3×200 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-3eed53b8d3844471b1a56d3a403dc497
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09265734B2

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