Reaktion #2266586

Reaktionsgleichung

water

product

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

lithium borohydride

→

(6-chloro-8-(phenylsulfonyl)-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridin-1-yl)methanol

Ausbeute 66.2%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe mixture was extracted with dichloromethane (3×10 mL)
2. 2
   TrocknenThe combined organic extracts were dried over anhydrous Na2SO4
3. 3
   Filtrationfiltered
4. 4
   Einengenthe filtrate concentrated in vacuo
5. 5
   SonstigeThe residue was purified by flash column chromatography (SiO2, 8:2 hexanes/ethyl acetate to ethyl acetate)

Vorschrift

To a stirred solution of the product of step D (51 mg, 0.12 mmol) in ethanol (5 mL) was added lithium borohydride (44 mg, 2.00 mmol) at ambient temperature. After 3 h, water (2 mL) was added and the mixture was extracted with dichloromethane (3×10 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and the filtrate concentrated in vacuo. The residue was purified by flash column chromatography (SiO2, 8:2 hexanes/ethyl acetate to ethyl acetate) to afford (6-chloro-8-(phenylsulfonyl)-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridin-1-yl)methanol (30 mg, 64%) as a brown oil: 1H NMR (CDCl3, 400 MHz) δ 8.01-7.94 (m, 3H), 7.82 (d, J=1.6 Hz, 1H), 7.57-7.50 (m, 3H), 4.23 (dd, J=4.0, 2.0 Hz, 1H), 3.95 (dd, J=11.2, 4.0 Hz, 1H), 3.77 (dd, J=10.8, 7.8 Hz, 1H), 3.31-3.17 (m, 2H), 2.84-2.81 (m, 2H).

Quelle