Diisobutylaluminum hydride → HCID 86651524, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of methyl 2-(tert-butyl-N-hydroxycarbamoyl)-isobutyrate (2.00 g) in dry CH2Cl2 (20 mL) at −78° C. under N2, 1M DIBAH in CH2Cl2 (17.14 mL) was added dropwise. The mixture was stirred at −78° C. for 3 hours and quenched by careful addition of MeOH (28 mL), Et2O (30 mL) and saturated aqueous solution of sodium potassium tartrate (30 mL). After 1 h the mixture was extracted three times with Et2O. The combined organic layers were washed with water, brine, dried over Na2SO4 and the solvent evaporated to dryness to give 2-(tert-butyl-N-hydroxycarbamoyl)-isobutyraldehyde (1.23 g, 71%). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 10.02 (1H, s), 9.58 (1H, s), 1.38 (9H, s), 1.17 (6H, s).

Provenance & Evidence