Acetic Acid → HCID 86596992, compound

HRID 1268890Notes

Reaction equation

[OH:1][C:2]1[CH:9]=[CH:8][C:7]([S:10][CH3:11])=[CH:6][C:3]=1[CH:4]=O.[CH3:12][C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][N:14]=1.[C:23](O)(=[O:25])[CH3:24].O>C(OC(=O)C)(=O)C>[C:23]([O:1][C:2]1[CH:9]=[CH:8][C:7]([S:10][CH3:11])=[CH:6][C:3]=1/[CH:4]=[CH:12]/[C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][N:14]=1)(=[O:25])[CH3:24]

Participants

Conditions

Temperature: 120 °C

Procedure

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+).

Workup

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

Sources & evidence

ORD record: ord-89e5749702224582a1b436230671a9a6
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07199140B2

Reaction notes

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