Reaktion #156277

Reaktionsgleichung

3-{4-[5-(tert-butyl-dimethyl-silanyloxymethyl)-4-methoxy-thiophen-2-ylmethoxy]-2-fluoro-phenyl}-propionicacid ethyl ester

tetra-n-butylammoniumfluoride

→

title compound

Ausbeute 108.6%

Ethyl 3-[2-fluoro-4-[[5-(hydroxymethyl)-4-methoxy-2-thienyl]methoxy]phenyl]propanoate

Ausbeute 108.6%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture is quenched with water
2. 2
   Sonstigeevaporated to a residue
3. 3
   ExtraktionThe residue is extracted with EtOAc
4. 4
   Waschenwashed with water (15 mL) and brine (15 mL)
5. 5
   Trocknendried over sodium sulfate
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated

Vorschrift

To a solution of 3-{4-[5-(tert-butyl-dimethyl-silanyloxymethyl)-4-methoxy-thiophen-2-ylmethoxy]-2-fluoro-phenyl}-propionicacid ethyl ester (0.5 g, 1.0 mmol) in THF (5 mL) is added tetra-n-butylammoniumfluoride (1M solution in THF, 2 mL, 2.0 mmol) at 0° C. and the reaction mixture is stirred for 30 minutes at 25° C. The reaction mixture is quenched with water and evaporated to a residue. The residue is extracted with EtOAc, washed with water (15 mL) and brine (15 mL), dried over sodium sulfate, filtered, and concentrated to give the title compound (0.4 g,). 1H NMR (400 MHz, DMSO d6) δ7.41 (s, 1H), 7.19-7.15 (t, J=8.8 Hz, 1H), 6.85-6.75 (m, 2H), 5.32 (br, 1H), 4.85 (s, 2H), 4.55 (s, 2H), 4.04-4.00 (q, J=7.2 Hz, 2H), 3.75 (s, 3H), 3.58 (s, 1H) 3.16-3.12 (t, J=15.2 Hz, 3H), 2.79-2.76 (t, J=14.8 Hz, 2H), 2.55-2.51 (t, J=15.2 Hz, 2H), 1.28-1.22 (t, J=7.2 Hz, 3H),

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