Methyl Methanesulfonate → Methyl (1-hydroxy-4-methyl-6-(tetrahydro-2H-pyran-2-yloxy)-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)methanesulfonate

HRID 1798320Notizen

Reaktionsgleichung

[CH3:1][S:2]([O:5][CH3:6])(=[O:4])=[O:3].[Li]CCCC.[CH3:12][C:13]1[CH:20]=[C:19]([O:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][O:23]2)[CH:18]=[C:17]([B:28]2[O:32]C(C)(C)[C:30](C)(C)[O:29]2)[C:14]=1C=O>C1COCC1>[OH:32][B:28]1[C:17]2[CH:18]=[C:19]([O:21][CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][O:23]3)[CH:20]=[C:13]([CH3:12])[C:14]=2[CH:30]([CH2:1][S:2]([O:5][CH3:6])(=[O:4])=[O:3])[O:29]1

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

To a cooled (−78° C.) solution of methyl methanesulfonate (1.56 mL, 20 mmol) in 15 ml anhydrous THF was added 1.6 M n-BuLi in hexanes (11.25 ml, 18 mmol) dropwise. The mixture was stirred at −78° C. for 20 minutes, then a solution of 2-methyl-4-(tetrahydro-2H-pyran-2-yloxy)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde (2.07 g, 6 mmol) in 15 mL THF was added slowly via syringe. After stirring at −78° C. for 10 minutes, the reaction was quenched with saturated ammonium chloride at −78° C. It was then extracted with EtOAc, washed with brine, dried over Na2SO4, and concentrated under reduced pressure to give crude product, which was purified by flash column. (1.64 g) MS (ESI) m/z=713 [2M+H]+.

Aufarbeitung

stirringAfter stirring at −78° C. for 10 minutes
customthe reaction was quenched with saturated ammonium chloride at −78° C
extractionIt was then extracted with EtOAc
washwashed with brine
dry with materialdried over Na2SO4
concentrationconcentrated under reduced pressure
customto give crude product, which
customwas purified by flash column

Quellen und Nachweise

ORD-Eintrag: ord-708cc1ee55eb4c0aa4104551103cf5b1
Quelldatensatz: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08343944B2

Notizen zur Reaktion

Wird geladen…