Water → 5-(1,3-Dioxolan-2-yl)-2-methylbenzofuran

HRID 2261108

Reaktionsgleichung

[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:7]=[CH:8][C:9]2[O:13][CH:12]=[CH:11][C:10]=2[CH:14]=1.[CH2:15]([Li])CCC.IC.O>C1COCC1.C(OCC)(=O)C>[CH3:15][C:12]1[O:13][C:9]2[CH:8]=[CH:7][C:6]([CH:2]3[O:3][CH2:4][CH2:5][O:1]3)=[CH:14][C:10]=2[CH:11]=1

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

5-[1,3]Dioxolan-2-yl-benzofuran (50 mg, 0.26 mmol) was dissolved in THF (2 mL) and the solution was cooled down to −78° C. Butyl lithium (180 uL, 1.1 eq.) was added dropwise. This mixture was stirred 30 min at 25° C. Then the reaction mixture was cooled down to −78° C. and iodomethane (18.1 uL, 1.1 eq.) dissolved in 1 mL THF was added dropwise to the reaction mixture. The temperature was increased slowly to room temperature overnight. Despite some starting material was detected, water and ethyl acetate were added to the mixture and the aqueous layer was extracted 3 times. Combined organic phases was dried over MgSO4, filtrated and evaporated to give 2-methyl-5-[1,3]dioxolan-2-yl-benzofuran (41.2 mg, 70%) sufficiently pure to be used in the next step.

Aufarbeitung

temperatureThen the reaction mixture was cooled down to −78° C.
additionwas added dropwise to the reaction mixture
temperatureThe temperature was increased slowly to room temperature overnight
extractionthe aqueous layer was extracted 3 times
dry with materialCombined organic phases was dried over MgSO4
filtrationfiltrated
customevaporated

Quellen und Nachweise

ORD-Eintrag: ord-d4dfb744593846dfa53119146824ee3a
Quelldatensatz: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07846925B2

Verknüpfte Notizen

Wird geladen…