Dimethylformamide → 2-(3-Formylphenyl)-2-isopropyl-1,3-dioxolane

HRID 2390068Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C:8]2([CH:13]([CH3:15])[CH3:14])[O:12][CH2:11][CH2:10][O:9]2)[CH:5]=[CH:6][CH:7]=1.C([Li])CCC.CN([CH:24]=[O:25])C.[Cl-].[NH4+]>C1COCC1>[CH:24]([C:2]1[CH:3]=[C:4]([C:8]2([CH:13]([CH3:15])[CH3:14])[O:12][CH2:11][CH2:10][O:9]2)[CH:5]=[CH:6][CH:7]=1)=[O:25]

Participants

Conditions

Temperature: -78 °C

Procedure

110 mg of 2-(3-bromophenyl)-2-isopropyl-1,3-dioxolane was dissolved in 1 mL of THF, and cooled to −78° C., and 0.36 mL of n-butyl lithium (1.5 M hexane solution) was added thereto, followed by stirring for 15 minutes. Thereafter, DMF (0.53 mL) was added thereto, followed by stirring at room temperature for 1 hour. A saturated aqueous ammonium chloride solution was added to the reaction liquid, followed by extraction with diethyl ether. The organic layer was then washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain 57 mg (yield 61%) of a title compound as a pale yellow oily substance.

Workup

stirringby stirring at room temperature for 1 hour
extractionfollowed by extraction with diethyl ether
washThe organic layer was then washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-46aa3fc1c3c84d16b736ca19a2b8b73a
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273766B2

Reaction notes

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