Triisopropyl borate → Boronic acid, (1-methylpropyl)-, bis(1-methylethyl) ester

HRID 1608375Notes

Reaction equation

[CH:1]([Li])([CH2:3][CH3:4])[CH3:2].[CH:6]([O:9][B:10](OC(C)C)[O:11][CH:12]([CH3:14])[CH3:13])([CH3:8])[CH3:7]>>[CH:1]([B:10]([O:11][CH:12]([CH3:14])[CH3:13])[O:9][CH:6]([CH3:8])[CH3:7])([CH2:3][CH3:4])[CH3:2]

Participants

Reactant 2

HCID 21531Triisopropyl borate

HCID 178418400CID 53628100

Product 1

HCID 13183021Boronic acid, (1-methylpropyl)-, bis(1-methylethyl) ester

Conditions

Temperature: 50 °C

Procedure

Following the method of Example 1, reaction of sec-butyllithium (208 mL, 250 mmol) and triisopropoxyborane (47.0 mL, 250 mmol), with solvents removed at 0° C. and 15 mm Hg and oil bath temperature maintained at 50° C., yielded sec-butyldiisopropoxyborane, 42.0 g (206 mmol, 90%), bp 138°-140° C. (754 mm Hg); proton NMR (neat) δ4.35 (septet, J=18 Hz, 2H), 1.09 (d, J=18 Hz, 12H), 0.8 (bm, 9H); boron NMR (neat) δ+79.5 ppm (s).

Workup

customwith solvents removed at 0° C.

Sources & evidence

ORD record: ord-8592839b0c824568bf2ea2379057e5e8
Source dataset: uspto-grants-1989_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04870212

Reaction notes

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