Sodium hydride → 2-(4-(2-Methoxyethoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 57521

Reaction equation

[CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[O:3]1.[H-].[Na+].[CH3:19][O:20][CH2:21][CH2:22]Br>CN(C=O)C>[CH3:19][O:20][CH2:21][CH2:22][O:15][C:12]1[CH:13]=[CH:14][C:9]([B:4]2[O:3][C:2]([CH3:16])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]2)=[CH:10][CH:11]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (150 mg, 0.682 mmol) in DMF (5 mL) was added 60% NaH (136 mg, 3.41 mmol) and 2-bromoethyl methyl ether (0.13 mL, 1.363 mmol). The resulting solution was stirred at 50° C. overnight, cooled to ambient temperature, quenched with water, and extracted with EtOAc. The combined extracts were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated. The residue was purified by flash chromatography to give the title compound (114 mg, 60% yield).

Workup

temperaturecooled to ambient temperature
customquenched with water
extractionextracted with EtOAc
washThe combined extracts were washed with brine
dry with materialdried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified by flash chromatography

Sources & evidence

ORD record: ord-54b3315cffc04387a3fc58752d298f1b
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434726B2

Linked notes

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