Toluene → N-[4-dimethylamino-2-butynyl)-2-hydroxy-2-methyl-2-phenylacetamide

HRID 1613295Notes

Reaction equation

[CH3:1][Mg]Br.[CH3:4][N:5]([CH3:21])[CH2:6][C:7]#[C:8][CH2:9][N:10](C(=O)C1C=CC=CC=1)[CH:11]=[O:12].[OH-:22].[Na+].[C:24]1([CH3:30])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(OCC)C.O1CCCC1>[CH3:21][N:5]([CH3:4])[CH2:6][C:7]#[C:8][CH2:9][NH:10][C:11](=[O:12])[C:30]([OH:22])([CH3:1])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of methylmagnesium bromide (10.23 m mol) in diethyl ether (3.5 ml) and tetrahydrofuran (5 ml) were added to a solution of N-(4-dimethylamino-2-butynyl)-benzoylformamide (0.50 g) in toluene (8 ml) at room temperature. After being heated at 70° C. for 1.5 hours, the mixture was treated with 1N aqueous solution of sodium hydroxide and extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel with a mixture of chloroform and methanol (15:1) as an eluent to give N-[4-dimethylamino-2-butynyl)-2-hydroxy-2-methyl-2-phenylacetamide (0.21 g).

Workup

extractionextracted with ethyl acetate
washThe extract was washed with brine
dry with materialdried over magnesium sulfate
customevaporated in vacuo
customThe residue was purified by column chromatography on silica gel with a mixture of chloroform and methanol (15:1) as an eluent

Sources & evidence

ORD record: ord-3eda1f4f6210492fac622d0358177308
Source dataset: uspto-grants-1993_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05192779

Reaction notes

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