Water → HCID 68874545, Verbindung

HRID 2224891Notizen

Reaktionsgleichung

[CH:1]1([CH2:7][C:8]([CH3:19])([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]([O:11]C)=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C[Si](C)(C)[O-].[K+].O>O1CCCC1>[CH:1]1([CH2:7][C:8]([CH3:19])([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:9]([OH:11])=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

Reaktionsbedingungen

Temperatur: 25 °C

Versuchsvorschrift

A solution of Example 41A (4.02 g, 15.4 mmol) and potassium trimethyl silanolate (11.0 g, 77.2 mmol) in tetrahydrofuran (80 mL) was heated to reflux for 18 hours. The mixture was cooled to 25° C., treated with water (10 mL), and concentrated in vacuo to remove the tetrahydrofuran. The residue was dissolved in water and washed with hexane. The aqueous layer was acidified to pH 1 with 1N hydrochloric acid and extracted three times with ethyl acetate. The ethyl acetate layers were combined, washed with brine, dried with sodium sulfate, filtered, and concentrated in vacuo to give the title compound (3.80 g, 99%). 1H NMR (300 MHz, CDCl3): δ ppm 1.10 m, 6 H) 1.57 m, 8 H) 1.82 m, 1 H) 2.04 m, 1 H) 7.32 m, 5 H).

Aufarbeitung

temperatureto reflux for 18 hours
concentrationconcentrated in vacuo
customto remove the tetrahydrofuran
dissolutionThe residue was dissolved in water
washwashed with hexane
extractionextracted three times with ethyl acetate
washwashed with brine
dry with materialdried with sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-0224621854e54ff2b09e4a4b83511a00
Quelldatensatz: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07378414B2

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