1-Cyclohexene-1-carboxaldehyde → HCID 11018877, compound

A 10 mL Schlenk flask was charged with bis(sulfonamide) ligand L*2 (3.8 mg, 0.01 mmol), Ti(OtBu)4 (193 □L, 0.50 mmol), and 0.5 mL hexanes and stirred for 30 min at room temp. A hexanes solution of Me2Zn (0.32 mL, 0.63 mmol) was then added, and after stirring for 10 min, cyclohexenecarboxaldehyde (28 □L, 0.25 mmol) was added. The reaction was stirred at room temp for 19 h and quenched with a saturated solution of aq NH4Cl. The organic and aqueous layers were separated, and the aqueous layer was extracted with hexanes (3×10 mL). The combined organic layers were then washed with brine and H2O and dried over MgSO4. The filtrate was concentrated in vacuo and the residue was chromatographed on silica (10% ethyl acetate in hexanes) to afford the title compound as a colorless oil in 94% yield (30 mg, 0.23 mmol). 1H NMR and 13C{1H} NMR spectra for this compound were identical to the previously reported literature data.

1. stirringThe reaction was stirred at room temp for 19 h
2. customquenched with a saturated solution of aq NH4Cl
3. customThe organic and aqueous layers were separated
4. extractionthe aqueous layer was extracted with hexanes (3×10 mL)
5. washThe combined organic layers were then washed with brine and H2O
6. dry with materialdried over MgSO4
7. concentrationThe filtrate was concentrated in vacuo
8. customthe residue was chromatographed on silica (10% ethyl acetate in hexanes)

ORD record

ord-29529057d38344e2b309b9d64b945999

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08236976B2