Reaktion #2260442

Reaktionsgleichung

(5-bromo-3,4-dihydro-1H-isochromen-1-yl)methanol

TMEDA

→

1-(hydroxymethyl)-3,4-dihydro-1H-isochromene-5-carbonitrile

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas microwaved 10 min at 100° C
2. 2
   SonstigeThe reaction was quenched with water
3. 3
   Extraktionextracted with EtOAc
4. 4
   WaschenThe organic layer was washed with brine
5. 5
   Sonstigedried
6. 6
   Einengenconcentrated
7. 7
   SonstigeThe residue was purified with prep-HPLC

Vorschrift

A mixture of (5-bromo-3,4-dihydro-1H-isochromen-1-yl)methanol (390 mg, 1.6 mmol), Zn(CN)2 (113 mg, 0.960 mmol), TMEDA (0.37 mg), xantphose (4.6 mg) and Pd(dba)3 (2.6 mg) in anhydrous DMF was microwaved 10 min at 100° C. The reaction was quenched with water and extracted with EtOAc. The organic layer was washed with brine, dried and concentrated. The residue was purified with prep-HPLC to give 1-(hydroxymethyl)-3,4-dihydro-1H-isochromene-5-carbonitrile. 1H-NMR (400 MHz, CDCl3) δ 7.49˜7.50 (m, 1H), 7.24˜7.48 (m, 2H), 4.76˜4.78 (in, 1H), 4.17˜4.22 (m, 1H), 3.76˜3.95 (m, 3H), 3.01˜3.09 (m, 1H), 2.89˜2.95 (m, 1H).

Quelle