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

HRID 1798320Notes

Reaction equation

[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

Participants

Conditions

Temperature: -78 °C

Procedure

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]+.

Workup

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

Sources & evidence

ORD record: ord-708cc1ee55eb4c0aa4104551103cf5b1
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08343944B2

Reaction notes

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