Reaktion #2266601

Reaktionsgleichung

product

6-chloro-1-(fluoromethyl)-2-(4-methoxybenzyl)-8-(phenylsulfonyl)-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridine

→

6-chloro-1-(fluoromethyl)-8-(phenylsulfonyl)-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridine

Ausbeute 12.0%

Lösungsmittel

water

acetone

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed sequentially with saturated aqueous NaHCO3 and brine
2. 2
   Trocknenthen dried over anhydrous MgSO4
3. 3
   FiltrationThe solution was filtered
4. 4
   Einengenthe filtrate concentrated in vacuo
5. 5
   Sonstigeto give the crude product which
6. 6
   Sonstigewas purified by flash column chromatography (SiO2, 9:1 to 1:1 hexanes/ethyl acetate)

Vorschrift

A solution of ceric ammonium nitrate (800 mg, 1.46 mmol) in water (1 mL) was added to a solution of the product obtained in step C (90 mg, 0.18 mmol) in acetone (10 mL). The resulting red solution was stirred at ambient temperature for 1.5 h, diluted with ethyl acetate, washed sequentially with saturated aqueous NaHCO3 and brine then dried over anhydrous MgSO4. The solution was filtered and the filtrate concentrated in vacuo to give the crude product which was purified by flash column chromatography (SiO2, 9:1 to 1:1 hexanes/ethyl acetate) providing 6-chloro-1-(fluoromethyl)-8-(phenylsulfonyl)-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridine (8 mg, 12%) as a colorless oil: 1H NMR (CDCl3, 300 MHz) δ 8.14 (d, J=1.5 Hz, 1H), 7.98-7.95 (m, 2H), 7.85 (d, J=1.8 Hz, 1H), 7.57-7.48 (m, 3H), 5.72-5.54 (m, 1H), 3.68-3.58 (m, 1H), 3.42-3.28 (m, 2H), 3.26-3.18 (m, 1H), 3.13-3.00 (m, 2H).

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