9-Borabicyclo(3.3.1)nonane → Trimethyl{[(3E)-2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-2-yl]oxy}silane
Reaction equation
[CH3:1][Si:2]([CH3:10])([CH3:9])[O:3][C:4]([CH3:8])([C:6]#[CH:7])[CH3:5].[CH3:11][C:12]1([CH3:19])[C:16]([CH3:18])([CH3:17])[O:15][BH:14][O:13]1.C12BC(CCC1)CCC2>O1CCCC1>[CH3:1][Si:2]([CH3:10])([CH3:9])[O:3][C:4]([CH3:8])(/[CH:6]=[CH:7]/[B:14]1[O:15][C:16]([CH3:18])([CH3:17])[C:12]([CH3:19])([CH3:11])[O:13]1)[CH3:5]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a solution of trimethyl(2-methylbut-3-yn-2-yloxy)silane (1.5 g, 9.60 mmol) in tetrahydrofuran (15 mL) was added 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.79 mL, 19.19 mmol), followed by addition of 9-BBN (9-borabicyclo[3.3.1]nonane) dimer (0.117 g, 0.480 mmol). This mixture was heated at 60° C. for 24 hours. The reaction was cooled and quenched carefully with saturated ammonium chloride solution. The reaction mixture was extracted with ethyl acetate (2×15 mL). The organics were combined, dried, concentrated and the residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-60% ethyl acetate in hexanes) to afford the title compound (600 mg, 22% yield). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.06-0.08 (m, 9H) 1.19 (s, 12H) 1.25 (s, 6H) 5.41 (d, J=17.85 Hz, 1H) 6.53 (d, J=17.85 Hz, 1H); MS (DCI/NH3) m/z 285 (M+H)+.
Workup
- temperatureThe reaction was cooled
- customquenched carefully with saturated ammonium chloride solution
- extractionThe reaction mixture was extracted with ethyl acetate (2×15 mL)
- customdried
- concentrationconcentrated
- customthe residue was purified by column chromatography
Sources & evidence
- ORD record
- ord-85e9449838ce4d5d8d0b1ddc377b054e
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08492371B2
Reaction notes
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