Hydrochloric Acid → 5-(2-Ethyl-[1,3]dioxolan-2-yl)thiophene-2-carbaldehyde

HRID 49327Notes

Reaction equation

[CH2:1]([C:3]1([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)[O:7][CH2:6][CH2:5][O:4]1)[CH3:2].C([Li])(C)(C)C.CN([CH:21]=[O:22])C.Cl>C1COCC1>[CH2:1]([C:3]1([C:8]2[S:9][C:10]([CH:21]=[O:22])=[CH:11][CH:12]=2)[O:4][CH2:5][CH2:6][O:7]1)[CH3:2]

Participants

Conditions

Temperature: -78 °C

Procedure

15 g (81.4 mmol) of 2-ethyl-2-2-thienyl-[1,3]dioxolane are dissolved in 300 mL of anhydrous THF and the mixture is then cooled to −78° C. 53 mL (89 mmol) of 1.7 M tert-butyllithium solution are then added, after which the reaction medium is stirred for 1 hour. 10 mL (120 mmol) of anhydrous DMF are then added and the medium is stirred for 1 hour. The reaction medium is treated at −78° C. with 1N hydrochloric acid solution and is then extracted with ethyl acetate and the organic phases are combined, dried and concentrated under reduced pressure. The residue obtained is purified by chromatography on a column of silica. A yellow oil is obtained (m=19 g; Y=100%).

Workup

stirringthe medium is stirred for 1 hour
extractionis then extracted with ethyl acetate
customdried
concentrationconcentrated under reduced pressure
customThe residue obtained
customis purified by chromatography on a column of silica
customA yellow oil is obtained (m=19 g; Y=100%)

Sources & evidence

ORD record: ord-b5d2b8c3abe54f9aab4ed54ff59fd55d
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06706725B1

Reaction notes

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