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

HRID 602026Notes

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-74326671ce66402e8d609e67137368f5
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902400B2

Reaction notes

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