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

HRID 2236378Notes

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].[H-].[Na+].O>CN(C=O)C>[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 solution of 5.0 g of 2-propynyl 3,4,5-trifluorobenzoate and 1.7 g of propargyl alcohol in 20 ml of DMF was added 1.1 g of 60% sodium hydride (oily) at 0° C. The mixture was stirred at 0° C. for 30 minutes and at room temperature for 1 hour. Then, water was added to the reaction mixture and the mixture was extracted 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 to obtain 2.9 g of 2-propynyl 3,5-difluoro-4-(2-propynyloxy)benzoate represented by the formula:

Workup

extractionthe mixture was extracted with ethyl acetate
dry with materialThe organic layer was dried over magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-04ba92852fe148409dc25e6b566eab19
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07714168B2

Reaction notes

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