Dimethylformamide → 2-Propynyl 3,5-difluoro-4-(2-propynyloxy)benzoate

HRID 1675580Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:11]=[C:12]([F:15])[C:13]=1F)[C:5]([O:7][CH2:8][C:9]#[CH:10])=[O:6].[CH2:16]([OH:19])[C:17]#[CH:18].CN(C=O)C.[H-].[Na+]>O>[F:15][C:12]1[CH:11]=[C:4]([CH:3]=[C:2]([F:1])[C:13]=1[O:19][CH2:16][C:17]#[CH:18])[C:5]([O:7][CH2:8][C:9]#[CH:10])=[O:6]

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture obtained by adding 5.0 g of 2-propynyl 3,4,5-trifluorobenzoate and 1.7 g of propargyl alcohol to 20 ml of DMF was added 1.1 g of 60% sodium hydride (oily) at 0° C. The resulting mixture was stirred at 0° C. for 30 minutes, and then at room temperature for 1 hour. Thereafter, water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and 2.9 g of 2-propynyl 3,5-difluoro-4-(2-propynyloxy)benzoate was obtained.

Workup

customTo a mixture obtained
waitat room temperature for 1 hour
extractionfollowed by extraction with ethyl acetate
dry with materialThe organic layer was dried over magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-55889d482b0441fab89b9318ff9c47f2
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08003699B2

Reaction notes

Loading…