Boron trifluoride → HCID 9998962, compound

HRID 1681913Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([C:15]2[N:19]=[C:18]([CH3:20])[O:17][N:16]=2)[CH:5]=[C:6]([CH3:14])[C:7]=1[O:8][CH2:9][CH2:10][CH2:11][C:12]#[CH:13].C([Li])CCC.[F:26][C:27]([F:34])([F:33])[C:28](OCC)=[O:29].B(F)(F)F>O1CCCC1>[CH3:1][C:2]1[CH:3]=[C:4]([C:15]2[N:19]=[C:18]([CH3:20])[O:17][N:16]=2)[CH:5]=[C:6]([CH3:14])[C:7]=1[O:8][CH2:9][CH2:10][CH2:11][C:12]#[C:13][C:28](=[O:29])[C:27]([F:34])([F:33])[F:26]

Participants

Conditions

Temperature: -70 °C

Procedure

A solution of 2.0 g 3-[3,5-dimethyl-4-(3-ethinylpropoxy)phenyl]-5-methyl-1,2,4-oxadiazole, prepared by a procedure similar to that described in Example 1(b), in 50 mls anhydrous tetrahydrofuran in an argon atmosphere was chilled to about -70° C. To this solution there was added 3.7 mls butyl lithium followed by ethyl trifluoroacetate and, after ten minutes, 1.5 mls boron trifluoride ethereate. The solution was stirred for five hours at -70° C. and then overnight without cooling, quenched with 20 mls aqueous ammonium chloride solution, diluted with water and extracted with ethyl ether. The ethyl ether extracts were dried (Na2SO4) and concentrated in vacuo. The residue was subjected to column chromatography (silica gel; 20:80 to 40:60 ethyl ether/hexane) to give 497 mg of the title compound as an oil.

Workup

temperatureovernight without cooling
customquenched with 20 mls aqueous ammonium chloride solution
additiondiluted with water
extractionextracted with ethyl ether
dry with materialThe ethyl ether extracts were dried (Na2SO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-9d1a958050e64957b56f06553fdc29a0
Source dataset: uspto-grants-1992_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05175177

Reaction notes

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