Acetic Acid → HCID 86596992, Verbindung

Temperatur

120 °C

2-hydroxy-5-methylsulfanylbenzaldehyde (5.05 g, 30 mmol) was dissolved in acetic anhydride (8 mL). Methyl 6-methylnicotinate (4.54 g, 30 mmol) and acetic acid (1.7 mL, 30 mmol) were added. The mixture was heated to 120° C. and stirred for 18 hours. The mixture was allowed to cool to room temperature before being poured into water (200 mL). The aqueous mixture was extracted with ethyl acetate (200 mL). The extract was washed with brine, dried over magnesium sulfate and concentrated in vacuo to afford a brown solid. This material was triturated with ethanol to give 6-[E-2-(-2-acetoxy-5-methylsulfanylphenyl)-vinyl]-nicotinic acid, methyl ester as a colourless solid (7.33 g, 71%) δH (300 MHz, DMSO-d6) 9.06 (1 H, d), 8.28 (1 H, dd), 7.77−7.68 (3 H, m), 7.50 (1 H, d), 7.27 (1 H, d), 7.15 (1 H, d), 3.86 (3 H, s), 2.55 (3 H, s), and 2.36 (3 H, s); m/z (ESI+) 344 (MH+).

1. temperatureto cool to room temperature
2. extractionThe aqueous mixture was extracted with ethyl acetate (200 mL)
3. washThe extract was washed with brine
4. dry with materialdried over magnesium sulfate
5. concentrationconcentrated in vacuo
6. customto afford a brown solid
7. customThis material was triturated with ethanol

ORD-Eintrag

ord-89e5749702224582a1b436230671a9a6

Quelldatensatz

uspto-grants-2007_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07199140B2