Water → 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1,4-dioxaspiro[4.5]dec-6-ene

HRID 337841

Reaktionsgleichung

I[C:2]1[C:3]2([CH2:8][CH2:9][CH2:10][CH:11]=1)[O:7][CH2:6][CH2:5][O:4]2.C([Li])CCC.[CH3:17][C:18]1([CH3:29])[C:22]([CH3:24])([CH3:23])[O:21][B:20](OC(C)C)[O:19]1.O>C1COCC1>[CH3:17][C:18]1([CH3:29])[C:22]([CH3:24])([CH3:23])[O:21][B:20]([C:2]2[C:3]3([CH2:8][CH2:9][CH2:10][CH:11]=2)[O:7][CH2:6][CH2:5][O:4]3)[O:19]1

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

To a solution of 6-iodo-1,4-dioxaspiro[4.5]dec-6-ene (Synlett, 2008, 1086-1090; 2.70 g, 10.2 mmol) in THF (30 mL), butyl lithium (1.65 M solution in hexane; 6.7 mL, 11.1 mmol) was added at −78° C. The reaction solution was stirred at −78° C. for 1 hour. Then, 4,4,5,5-tetramethyl-2-(propan-2-yloxy)-1,3,2-dioxaborolane (4.0 mL, 19.8 mmol) was added thereto, and the mixture was stirred at −78° C. for 2 hours. To the reaction solution, water (50 mL) was added, followed by extraction with ethyl acetate (50 mL). The thus obtained organic layer was dried over anhydrous sodium sulfate. After vacuum concentration, the residue was purified with silica gel chromatography (hexane/ethyl acetate=9:1) to yield the title compound (1.52 g, 56%) as a colorless oil.

Aufarbeitung

stirringthe mixture was stirred at −78° C. for 2 hours
extractionfollowed by extraction with ethyl acetate (50 mL)
dry with materialThe thus obtained organic layer was dried over anhydrous sodium sulfate
concentrationAfter vacuum concentration
customthe residue was purified with silica gel chromatography (hexane/ethyl acetate=9:1)

Quellen und Nachweise

ORD-Eintrag: ord-beb2518ec90842ddbc94d74f4d5a8283
Quelldatensatz: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08889741B2

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