Réaction #48923

Équation de réaction

KH2PO4

Potassium t-butoxide

4-chloro-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one

2,6-dichloro-3-methylaniline

→

8-(cyclopentyloxy)-4-(2,6-dichloro-3-methylphenylamino)-7-methoxy-2H-chromen-2-one

Solvants

DMSO

Conditions de réaction

Traitement

1. 1
   Extractionextracted with ethyl acetate (20 mL×2)
2. 2
   AutreThe combined extracts were dried
3. 3
   Filtrationfiltered
4. 4
   Concentrationconcentrated
5. 5
   Autrepurified by silica gel chromatography (4:1→0:1; hexanes:ethyl acetate)

Mode opératoire

Potassium t-butoxide (35 mg, 0.3 mmol) was added to a solution of 4-chloro-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one (29 mg, 0.1 mmol, Example 7, Step 1), 2,6-dichloro-3-methylaniline (26 mg, 0.15 mmol), and DMSO (1 mL). After 14 h, the reaction was poured into 1M KH2PO4 (20 mL), and extracted with ethyl acetate (20 mL×2). The combined extracts were dried, filtered, concentrated, and purified by silica gel chromatography (4:1→0:1; hexanes:ethyl acetate) to give 8-(cyclopentyloxy)-4-(2,6-dichloro-3-methylphenylamino)-7-methoxy-2H-chromen-2-one: 1H NMR (400 MHz, DMSO-d6): δ 9.38 (s, 1H), 7.95 (d, 1H), 7.58 (d, 1H), 7.48 (d, 1H), 7.18 (d, 1H), 4.82 (m, 1H), 4.33 (s, 1H), 3.90 (s, 3H), 2.40 (s, 3H), 1.90-1.45 (m, 8H); MS (ESI): 433.9.

Source