Diisobutylaluminum hydride → HCID 11062610, compound

Temperature

-78 °C

To a solution of 12.00 g (65.93 mmol) of <(E)-methyl-4-cyclohexyl-2-butenoate dissolved in 400 mL of diethyl ether cooled to -78° C. was added 215 mL (215 mmol) of DIBAL-H (1.0M in THF). After 0.5 hr the reaction was warmed to 0° C. for 0.5 hr and quenched with 300 mL of aqueous saturated solution of NaK tartrate, this stirred for 14 hr. The aqueous layer was extracted with ether (2×100 mL) and the combined organic layers were washed with water (1×100 mL), brine (1×100 mL), dried over MgSO4 and concentrated to provide (E)-4-cyclohexyl-2-buten-1-ol as colorless oil.

1. temperatureAfter 0.5 hr the reaction was warmed to 0° C. for 0.5 hr
2. customquenched with 300 mL of aqueous saturated solution of NaK tartrate
3. extractionThe aqueous layer was extracted with ether (2×100 mL)
4. washthe combined organic layers were washed with water (1×100 mL), brine (1×100 mL)
5. dry with materialdried over MgSO4
6. concentrationconcentrated

ORD record

ord-4591f898090c46a0aeb9617801ea593d

Source dataset

uspto-grants-1996_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05502053