Diethyl Ether → HCID 86706873, compound

HRID 717894Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6](I)[CH:5]=[C:4]([C:9]([F:12])([F:11])[F:10])[N:3]=1.C([Mg]Cl)(C)C.C(OCC)C.[O:23]1[CH2:26][C:25](=[O:27])[CH2:24]1>O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]([C:25]2([OH:27])[CH2:26][O:23][CH2:24]2)[CH:5]=[C:4]([C:9]([F:12])([F:11])[F:10])[N:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2-chloro-4-iodo-6-(trifluoromethyl)pyridine (1.00 g, 3.25 mmol, European Journal of Organic Chemistry, (18), 3793-3798, 2004) in tetrahydrofuran (20 mL) at 0° C. was added dropwise 2.0 M isopropylmagnesium chloride in diethyl ether (1.95 mL, 3.90 mmol, Aldrich). After stirring for 30 minutes at 0° C., a solution of oxetan-3-one (0.281 g, 3.90 mmol, Synthonix) in Tetrahydrofuran (5 mL) was added. After stirring for 1 hour, the reaction was quenched by the addition of water and ammonium chloride. The product was extracted with two portions of ethyl acetate. The combined organic extracts were dried over sodium sulfate, filtered and concentrated. Flash chromatography, eluting with a gradient from 0-40% EtOAc in hexanes on a 40 g silica gel cartridge afforded purified product (0.31 g, 38%). LCMS (M+H)+: 254.1.

Workup

stirringAfter stirring for 1 hour
customthe reaction was quenched by the addition of water and ammonium chloride
extractionThe product was extracted with two portions of ethyl acetate
dry with materialThe combined organic extracts were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated
washFlash chromatography, eluting with a gradient from 0-40% EtOAc in hexanes on a 40 g silica gel cartridge
customafforded
custompurified product (0.31 g, 38%)

Sources & evidence

ORD record: ord-3c25f68e0f804c6f81c5b123a29c367a
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193733B2

Reaction notes

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