Hydrochloric Acid → (+/-)-4-(Prop-2-en-1-yloxy)pent-1-en-3-one

HRID 242019Notes

Reaction equation

CON(C)[C:4](=[O:11])[CH:5]([O:7][CH2:8][CH:9]=[CH2:10])[CH3:6].[CH:13]([Mg]Br)=[CH2:14].Cl>O1CCCC1>[CH2:8]([O:7][CH:5]([CH3:6])[C:4](=[O:11])[CH:13]=[CH2:14])[CH:9]=[CH2:10]

Participants

Conditions

Temperature: -78 °C

Procedure

(±)-N-Methoxy-N-methyl-2-(prop-2-en-1-yloxy)propanamide (1.26 g, 7.27 mmol) was dissolved in tetrahydrofuran (20 mL) and cooled to −78° C. Vinylmagnesium bromide (11.4 mL, 0.7 M solution in tetrahydrofuran, 8.00 mmol, 1.1 equiv) was added and the mixture was stirred at −78° C. for 10 minutes. Hydrochloric acid (5 mL, 4 M aqueous) was added, the mixture was warmed to ambient temperature and extracted with chloroform (2×30 mL). The combined organic extracts were dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel gradient chromatography (100:0 to 30:70; hexanes:ethyl acetate), providing the titled compound.

Workup

temperaturethe mixture was warmed to ambient temperature
extractionextracted with chloroform (2×30 mL)
dry with materialThe combined organic extracts were dried with sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by silica gel gradient chromatography (100:0 to 30:70; hexanes:ethyl acetate)

Sources & evidence

ORD record: ord-e2119f75af6f47bd943605c48b41b578
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653079B2

Reaction notes

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