Water → 2-Chloro-5-(1,3-dioxolan-2-yl)benzofuran

HRID 2261106

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.C([Li])CCC.C1C(=O)N([Cl:27])C(=O)C1.O>C1COCC1.C(OCC)(=O)C>[Cl:27][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 TIE (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 NCS (39 mg, 1.1 eq.) dissolved in 1 mL THF was added dropwise to the reaction mixture. After 1 h30 at −78° C. only small amount of starting material could be detected. The temperature was increased slowly to room temperature overnight. 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-Chloro-5-[1,3]dioxolan-2-yl-benzofuran (48.1 mg, 81%) 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
customat −78° C.
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-fa8783c398214a318d539fbff946e87b
Quelldatensatz: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07846925B2

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