Hydrochloric Acid → HCID 14559528, compound

HRID 1657204Notes

Reaction equation

CN(P(N(C)C)(N(C)C)=O)C.[CH3:12][C:13]1([CH3:21])[O:18][C:17](=[O:19])[CH:16]=[C:15]([CH3:20])[O:14]1.[CH:22]([C:24]([CH3:26])=[O:25])=[CH2:23].Cl>CCOCC>[CH3:12][C:13]1([CH3:21])[O:18][C:17](=[O:19])[CH:16]=[C:15]([CH2:20][CH2:23][CH2:22][C:24](=[O:25])[CH3:26])[O:14]1

Participants

Conditions

Temperature: -78 °C

Procedure

In an argon gas stream, 20.6 ml of n-butyl lithium (1.6M solution in hexane) were added to 60 ml of an ether solution containing 3.53 g (0.033 mol) of diisopropylamine at -20° C. to form LDA. After stirring for 30 minutes, the solution was cooled to -78° C., and 10.4 ml (0.06 mol) of HMPA were added thereto, followed by stirring for 15 minutes. Afterward, a mixture of 4.26 g (0.03 mol) of 2,2-dimethyl-6-methyl-1,3-dioxin-4-one and 60 ml of ether as well as 60 ml of an ether solution containing 2.1 g (0.03 mol) of methyl vinyl ketone were added to the solution. After the temperature was gradually returned to room temperature, 10% hydrochloric acid was added thereto to neutralize the solution, and extraction was then carried out with ether. The resultant organic layer was dried over anhydrous magnesium sulfate. Next, the used solvent was distilled off, and the residue was then subjected to column chromatography (an eluent of hexane:ethyl acetate=4:1), thereby obtaining 3.16 g of 2,2-dimethyl-6-(4-oxopentyl)-1,3-dioxin-4-one.

Workup

stirringby stirring for 15 minutes
additionwere added to the solution
customwas gradually returned to room temperature
extractionthe solution, and extraction
dry with materialThe resultant organic layer was dried over anhydrous magnesium sulfate
distillationNext, the used solvent was distilled off

Sources & evidence

ORD record: ord-d69404dd334d44c79842114f0caa1678
Source dataset: uspto-grants-1993_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05256800

Reaction notes

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