Réaction #681956

Équation de réaction

7-Bromochroman-4-one

thiophene-2-thiol

potassium carbonate

→

title compound

Rendement 93.0%

7-(thiophen-2-ylsulfanyl)-3,4-dihydro-2H-1-benzopyran-4-one

Rendement 93.0%

Solvants

ACN

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction was cooled
2. 2
   Filtrationfiltered
3. 3
   Concentrationconcentrated
4. 4
   AutrePurification by silica gel chromatography (10-60% EtOAc/hexanes)

Mode opératoire

7-Bromochroman-4-one (1.5 g, 6.6 mmol), thiophene-2-thiol (0.68 mL, 7.3 mmol), and potassium carbonate (1.37 g, 9.9 mmol) were combined in ACN (50 mL) in a sealed vessel, and the reaction was heated at 78° C. overnight. The reaction was cooled, filtered, and concentrated. Purification by silica gel chromatography (10-60% EtOAc/hexanes) gave 1.6 g (93%) of the title compound as a yellow oil. 1H NMR (400 MHz, DMSO-d6): δ 2.75 (2H, t, J=6.4 Hz), 4.48 (2H, t, J=6.4 Hz), 6.59 (1H, d, J=1.8 Hz), 6.75 (1H, dd, J=8.4, 1.8 Hz), 7.13-7.17 (1H, m), 7.34 (1H, dd, J=3.6, 1.2 Hz), 8.58 (1H, dd, J=5.4, 1.2 Hz), 7.75 (1H, d, J=8.4 Hz). [M+H] calc'd for C13H10O2S2, 263. found 263.

Source