Dimethylformamide → 3-(2-Ethyl-1,3-dioxolan-2-yl)benzaldehyde

HRID 644563Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C:8]2([CH2:13][CH3:14])[O:12][CH2:11][CH2:10][O:9]2)[CH:5]=[CH:6][CH:7]=1.C([Li])CCC.CN([CH:23]=[O:24])C.[Cl-].[NH4+]>C1COCC1>[CH2:13]([C:8]1([C:4]2[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=2)[CH:23]=[O:24])[O:12][CH2:11][CH2:10][O:9]1)[CH3:14]

Participants

Conditions

Temperature: -78 °C

Procedure

17.8 g (70 mmol) of 2-(3-bromophenyl)-2-ethyl-[1,3]dioxolane are dissolved in 300 ml of THF and the mixture is cooled to −78° C. 34 ml (85 mmol) of a 2.5 M solution of butyllithium are added slowly, and the mixture is stirred for 30 minutes. 8.1 ml (105 mmol) of DMF are then added, and the mixture is brought back to 0° C., then treated with a saturated solution of ammonium chloride. After extraction with ethyl ether, the desired aldehyde is obtained in the form of yellow oil (m=14 g; Y=97%).

Workup

customis brought back to 0° C.
extractionAfter extraction with ethyl ether

Sources & evidence

ORD record: ord-ac7a3770a7d74a3da11932c77d1f80bf
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07700657B2

Reaction notes

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