Water → 2-[2-(Tert-butyldimethylsilanyloxy)-ethyl]-furan-3-yl-boronic acid

HRID 1778359Notes

Reaction equation

C([Li])CCC.Br[C:7]1[CH:11]=[CH:10][O:9][C:8]=1[CH2:12][CH2:13][O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16].C[O:23][B:24](OC)[O:25]C.O>C(OCC)C>[Si:15]([O:14][CH2:13][CH2:12][C:8]1[O:9][CH:10]=[CH:11][C:7]=1[B:24]([OH:25])[OH:23])([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]

Participants

Conditions

Temperature: 0 °C

Procedure

n-Butyllithium (2.5M in hexanes, 5.78 mL) was added to a solution of [2-(3-bromofuran-2-yl)-ethoxy]-tert-butyldimethylsilane (Intermediate 34, 4.01 g) in diethyl ether (130 mL) at −60° C. under nitrogen and the resultant mixture was stirred for 30 minutes. Trimethylborate (2.73 g) was then added to the mixture and it was stirred for a further 10 minutes. The reaction mixture was warmed to 0° C., water was added and the mixture was stirred for 15 minutes. The organic layer was separated, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-30% to give 2-[2-(tert-butyldimethylsilanyloxy)-ethyl]-furan-3-yl-boronic acid (1.23 g) as a colourless oil.

Workup

stirringthe mixture was stirred for 15 minutes
customThe organic layer was separated
dry with materialdried (MgSO4)
filtrationfiltered
customThe filtrate was evaporated to dryness
customthe residue was purified by chromatography on silica
washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-30%

Sources & evidence

ORD record: ord-0ecf48c4b3e54337820c9a1514b02f01
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266896B2

Reaction notes

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