Reaktion #220614

Reaktionsgleichung

3-(4-chlorophenyl)-2-phenylpropionic acid

3-(4-Chlorophenyl)-2-phenylpropanoic acid

oxalyl chloride

N-methoxy-N-methylamine hydrochloride

triethyl amine

→

crude product

N-Methoxy-N-methyl-3-(4-chlorophenyl)-2-phenylpropanamide

Lösungsmittel

ether

CH2Cl2

dimethyl formamide

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenconcentrated to dryness
2. 2
   Sonstigeto give the crude acyl chloride, which
3. 3
   Sonstigewas used without further purification
4. 4
   Waschensuccessively washed with water, dilute aqueous sodium hydrogen sulfate and brine
5. 5
   Trocknendried over anhydrous MgSO4
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated to dryness

Vorschrift

To a solution of 3-(4-chlorophenyl)-2-phenylpropionic acid (Step B, 14 g, 55 mmol) in CH2Cl2 (125 mL) at 0° C. was added dimethyl formamide (50 μL) and oxalyl chloride (14 g, 0.11 mol) dropwise. The reaction was allowed to warm to room temperature overnight and concentrated to dryness to give the crude acyl chloride, which was used without further purification. Thus, to a solution of the acyl chloride in CH2Cl2 (250 mL) was added N-methoxy-N-methylamine hydrochloride (11 g, 0.11 mol) and triethyl amine (dried over activated molecular sieves, 30 mL, 0.22 mol) at 0° C. After stirring at room temperature for 4 h, the reaction mixture was diluted with ether (500 mL) and successively washed with water, dilute aqueous sodium hydrogen sulfate and brine, dried over anhydrous MgSO4, filtered and concentrated to dryness to give the crude product, which was used without further purification. 1H NMR (500 MHz, CD3OD): δ 7.4-7.1 (m, 9H), 4.38 (br, 1H), 3.48 (s, 3H), 3.35 (dd, 1H), 3.10 (s, 3H), 2.92 (dd, 1H); LC-MS: m/e 304 (3.6 min).

Quelle