Water → 4-Methyl-6-[4-(methylthio)phenyl]-2-pyridone

HRID 268594

Reaction equation

C([N-]C(C)C)(C)C.[Li+].[CH3:9][C:10]([CH3:15])=[CH:11][C:12](O)=[O:13].[CH3:16][S:17][C:18]1[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=1.O>CCCCCCC.C1COCC1.C(C1C=CC=CC=1)C.C1COCC1.C(OCC)(=O)C>[CH3:9][C:10]1[CH:15]=[C:22]([C:21]2[CH:24]=[CH:25][C:18]([S:17][CH3:16])=[CH:19][CH:20]=2)[NH:23][C:12](=[O:13])[CH:11]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of lithium diisopropylamide (50 mL of a 2M solution in heptane/THF/ethyl benzene, 0.1 mol) in THF (50 mL) at −78° C. and under an atmosphere of nitrogen was added dropwise a solution of 3-methyl-2-butenoic acid (5 g, 0.05 mol) in THF (50 mL). The reaction was warmed to 0° C. for 30 minutes. After cooling to −78° C., a solution of 4-(methylthio)benzonitrile (7.45 g, 0.05 mol) in THF (50 mL) was added dropwise. Upon complete addition, the reaction was warmed to room temperature and stirred for 3 hours. Water (150 mL) and ethyl acetate (100 mL) were added to the reaction mixture and the resulting precipitate filtered, washed with ethyl acetate and dried to give the title compound (4.96 g, 43%) LC retention time 2.75 mins, MS m/z 232 (MH+).

Workup

temperatureAfter cooling to −78° C.
additionUpon complete addition
temperaturethe reaction was warmed to room temperature
filtrationthe resulting precipitate filtered
washwashed with ethyl acetate
customdried

Sources & evidence

ORD record: ord-aac106cf1a6c405b905ea34475681619
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07446117B2

Linked notes

Loading…