Triisopropyl borate → Dipropan-2-yl tert-butylboronate
Reaction equation
[C:1]([Li])([CH3:4])([CH3:3])[CH3:2].[CH:6]([O:9][B:10](OC(C)C)[O:11][CH:12]([CH3:14])[CH3:13])([CH3:8])[CH3:7]>C(OCC)C>[C:1]([B:10]([O:11][CH:12]([CH3:14])[CH3:13])[O:9][CH:6]([CH3:8])[CH3:7])([CH3:4])([CH3:3])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
The reaction was conducted as described in Example 1 with tert-butyllithium (30.9 mL, 51 mmol) which was added to triisopropoxyborane (9.59 mL, 51 mmol) in 51 mL ethyl ether cooled to -100° C. instead of -78° C. Solvents were removed at 0° C. and 15 mm Hg. The oil bath was maintained at 50° C. to furnish tert-butyldiisopropoxyborane: 8.44 g (45.3 mmol, 89%), bp 136°-138° (754 mm Hg); proton NMR (neat)δ+4.50 (septet, J=18 Hz, 2H), 1.12 (d, J=18 Hz, 12H), 0.95 (s, 9H); boron NMR (neat) δ+29.5 ppm (s).
Workup
- customSolvents were removed at 0° C.
- temperatureThe oil bath was maintained at 50° C.
Sources & evidence
- ORD record
- ord-4fe53f615b194e36a98d26ca4ebf9720
- Source dataset
- uspto-grants-1989_09
- Patent number
- US04870177
Reaction notes
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