Reaktion #546339

Reaktionsgleichung

2-(3-Fluoro-4-methoxy-phenyl)-[1,3]-dioxolane

Sodium thiomethoxide

ammonium chloride

→

4-[1,3]dioxolan-2-yl-2-fluoro-phenol

Ausbeute 52.0%

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe aqueous layer extracted with methylene chloride (4×10 mL)
2. 2
   TrocknenThe combined organic layers were dried (Na2SO4)
3. 3
   Filtrationfiltered
4. 4
   Einengenconcentrated under vacuum
5. 5
   SonstigeThe residue was chromatographed (silica gel, hexanes/ethyl acetate 7:3)

Vorschrift

A solution of 2-(3-Fluoro-4-methoxy-phenyl)-[1,3]-dioxolane (250 mg, 1.26 mmol) and Sodium thiomethoxide (106 mg, 1.51 mmol) in dry N,N-dimethylformamide (3.5 mL) was heated at 100° C. under nitrogen for 4 hours. Then a saturated solution of ammonium chloride (15 mL) was added and the aqueous layer extracted with methylene chloride (4×10 mL). The combined organic layers were dried (Na2SO4), filtered and concentrated under vacuum. The residue was chromatographed (silica gel, hexanes/ethyl acetate 7:3) to produce 4-[1,3]dioxolan-2-yl-2-fluoro-phenol as a pale brown oil (120 mg, 52%). 1H-NMR (CDCl3, 200.15 MHz): δ 7.24–7.01 (m, 2H), 6.88 (t, 1H, J=8.4), 6.07 (sa, 1H), 5.71 (s, 1H), 4.13–3.95 (m, 4H).

Quelle