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

A 10 mL Schlenk flask was charged with bis(sulfonamide) ligand 2 (3.8 mg, 0.01 mmol), Ti(OtBu)4 (193 μL, 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 μL, 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. 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 (CDCl3, 500 MHz) δ.1.20 (d, 3H, J=6.2 Hz), 1.51 (m, 4H), 1.61 (br s, 1H), 1.99 (m, 4H), 4.10 (q, 1H, J=6.2 Hz), and 5.61 (br t, 1H) ppm; 13C{1H} NMR (CDCl3; 125 MHz) δ.21.4, 22.5, 22.6, 23.6, 24.8, 72.0, 121.3, and 141.2 ppm. 1H NMR and 13C NMR spectra for this compound compare with previously reported literature data.

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

ORD record

ord-0e6620f840a64442825168fa450cab0e

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08236976B2