Diisobutylaluminum hydride → 304004-77-1

Temperature

-78 °C

To a solution of methyl 2-(tert-butyldimethylsilyloxy)-2-methylpropanoate (1.00 g, 4.30 mmol) in hexanes (15 mL) at about −78° C. was added DIBAL-H (1.0 M in hexanes, 9.47 mL, 9.47 mmol) drop-wise over about 5 min. The solution was stirred at about −78° C. for about 5 min and the cooling bath was removed. The solution was warmed to ambient temperature and stirred for about 1 h. The reaction was then re-cooled to about 0° C. and was quenched with the slow addition of a saturated solution of sodium potassium tartrate (about 20 mL). The thick suspension was stirred at ambient temperature for about 2 h until the two layers were clear. The layers were separated and the aqueous layer was extracted with DCM (2×50 mL). The combined organic extracts were washed with water and brine, dried over MgSO4, filtered, and the solvents were removed under reduced pressure to give as the title compound (0.73 g, 83%) as a colorless oil: 1H NMR (CDCl3) δ 3.32 (s, 2H), 1.24 (s, 6H), 0.88 (d, J=2.9, 9H), 0.12 (d, J=3.2, 6H).

1. customthe cooling bath was removed
2. temperatureThe solution was warmed to ambient temperature
3. stirringstirred for about 1 h
4. temperatureThe reaction was then re-cooled to about 0° C.
5. customwas quenched with the slow addition of a saturated solution of sodium potassium tartrate (about 20 mL)
6. stirringThe thick suspension was stirred at ambient temperature for about 2 h until the two layers
7. customThe layers were separated
8. extractionthe aqueous layer was extracted with DCM (2×50 mL)
9. washThe combined organic extracts were washed with water and brine
10. dry with materialdried over MgSO4
11. filtrationfiltered
12. customthe solvents were removed under reduced pressure

ORD record

ord-739f85f987d6469f83b4002c25118821

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08188083B2