Water → 1,1-Dimethylethyl 2-cyanobutanoate

HRID 1481047Notes

Reaction equation

[C:1]([O:5][C:6](=[O:10])[CH2:7][C:8]#[N:9])([CH3:4])([CH3:3])[CH3:2].[CH2:11]1CCN2C(=NCCC2)C[CH2:12]1.ICC.O>CN(C=O)C.CCOC(C)=O>[C:1]([O:5][C:6](=[O:10])[CH:7]([C:8]#[N:9])[CH2:11][CH3:12])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of cyanoacetic acid tert-butyl ester (10.0 mL, 69.99 mmoL) (TCI America, Portland Oreg.) and DBU (10.5 mL, 69.99 mmol) in DMF (70 mL) was added iodoethane (6.8 mL, 84.00 mmol) dropwise at 0° C. The resulting mixture was heated to 70° C. for 20 hours. After cooling to room temperature, H2O (350 mL) and EtOAc (350 mL) were added. The layers were separated and the aqueous layer was extracted twice with EtOAc. The combined organic layers were dried over MgSO4, concentrated, and purified by flash chromatography (0-30% EtOAc/hexanes) to give the title compound in 5 g. 1H NMR (CDCl3, 200 MHz): δ=3.36 (dd, 1H, J=6.3 Hz and 6.3 Hz), 2.06-1.88 (m, 2H), 1.49 (s, 9H), 1.11 (t, 3H, J=7.3 Hz).

Workup

temperatureAfter cooling to room temperature
customThe layers were separated
extractionthe aqueous layer was extracted twice with EtOAc
dry with materialThe combined organic layers were dried over MgSO4
concentrationconcentrated
custompurified by flash chromatography (0-30% EtOAc/hexanes)

Sources & evidence

ORD record: ord-907a4dcde5d74a5c9a3c5185fad0ad2b
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409892B2

Reaction notes

Loading…