Toluene → HCID 68912698, compound

Temperature

0 °C

A 10 mL Schlenk flask was charged with 3.5 mg (0.015 mmol) (−)-MIB and a stir bar. Under a nitrogen atmosphere in a glovebox, the di(2-methyl-propene)zinc reagent (89.5 mg, 0.51 mmol) was weighed and added to the Schlenk flask. Toluene (1.5 mL) was added, followed by 3.1 equiv Et2Zn (115 μL, 1.13 mmol). After cooling to 0° C., cyclohexanecarboxaldehyde (40.8 mg, 0.36 mmol) was added dropwise. After the reaction was complete (2 h), it was quenched with saturated aq NH4Cl. The organic and aqueous layers were separated and the aqueous layer was extracted with diethyl ether (3×25 mL). The combined organic layers were washed with brine, dried over MgSO4 and concentrated. The crude product was purified by column chromatography on silica (70:20:10, hexanes:CH2Cl2:EtOAc) to afford the title compound as a colorless oil in 75% yield (45.8 mg, 0.27 mmol). 1H NMR and 13C{1H} NMR spectra for this compound were identical to the previously reported literature data.

1. additionA 10 mL Schlenk flask was charged with 3.5 mg (0.015 mmol) (−)-MIB and a stir bar
2. additionadded to the Schlenk flask
3. custom(2 h), it
4. customwas quenched with saturated aq NH4Cl
5. customThe organic and aqueous layers were separated
6. extractionthe aqueous layer was extracted with diethyl ether (3×25 mL)
7. washThe combined organic layers were washed with brine
8. dry with materialdried over MgSO4
9. concentrationconcentrated
10. customThe crude product was purified by column chromatography on silica (70:20:10, hexanes:CH2Cl2:EtOAc)

ORD record

ord-9e1c5cf1cfe746c0a055d3eb12137605

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08236976B2