Dimethylformamide → HCID 22734350, compound

HRID 2084818Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:5]([O:7][CH3:8])=[O:6].Cl[C:15]([CH3:19])([CH3:18])[C:16]#[CH:17].C(=O)([O-])[O-].[Cs+].[Cs+].CN(C=O)C>O>[CH3:18][C:15]([CH3:19])([O:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:5]([O:7][CH3:8])=[O:6])[C:16]#[CH:17]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of methyl 3-hydroxy-4-methoxybenzoate (5.41 g), 3-chloro-3-methyl-1-butyne (10 ml), cesium carbonate (19.4 g), and DMF (54 ml) was stirred at 80° C. for one hour. 3-Chloro-3-methyl-1-butyne (5 ml) was further added to the mixture followed by stirring at 90° C. for 3 hours. After being allowed to stand for cooling, water was added to the mixture followed by extraction with ether. The organic layer was washed with a 1N aqueous solution of sodium hydroxide and with a saturated saline and dried over sodium sulfate, and the solvent was distilled off. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1 and 7/1) to give Compound IIao-a (2.31 g, 31%) as a brown oily substance.

Workup

stirringby stirring at 90° C. for 3 hours
temperaturefor cooling
extractionfollowed by extraction with ether
washThe organic layer was washed with a 1N aqueous solution of sodium hydroxide and with a saturated saline
dry with materialdried over sodium sulfate
distillationthe solvent was distilled off
customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1 and 7/1)
customto give Compound IIao-a (2.31 g, 31%) as a brown oily substance

Sources & evidence

ORD record: ord-c0c7e29095494e19886880ffc5008f6d
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06716987B1

Reaction notes

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