Propanoic acid, 2-Diazo-, 2-methyl-1-(1-methylethyl)propyl ester

Abstract

Propanoic acid, 2-Diazo-, 2-methyl-1-(1-methylethyl)propyl ester [1318778-97-0] C10H18N2O2 (MW 198.26) InChI = 1S/C10H18N2O2/c1-6(2)9(7(3)4)14-10(13)8(5)12-11/h6-7,9H,1-5H3 InChIKey = XJZKHHMPGIMIID-UHFFFAOYSA-N (used as a carbene precursor in a range of asymmetric reactions, including cyclopropenation,1 cyclopropanation,2 CH functionalization,3 and CH insertion processes4) Alternate Name: 2,4-dimethyl-3-pentyl α-diazopropionate. Physical Data: 1H NMR (400 MHz, CDCl3) δ 0.86 (d, J = 6.8 Hz, 6H), 0.90 (d, J = 6.8 Hz, 6H), 1.86–1.95 (m, 2H), 1.98 (s, 3H), 4.62 (t, J = 6.3 Hz, 1H); IR (neat): 2967, 2254, 2080, 1683, 1464, 1372, 1312, 1152, 1127, 908, 732 cm−1. Solubility: soluble in most organic solvents including hydrocarbons. Form Supplied in: not commercially available. Preparative Method: by the reaction of 2,4-dimethyl-3-pentanol with diketene followed by methylation and deacylative diazo transfer.5 Purification: column chromatography on silica gel using hexane/diethyl ether (40:1) as a solvent to give the title compound as a yellow oil. Handling, Storage, and Precautions: the title compound should be kept under an inert atmosphere and stored under refrigeration. No difficulty in handling of this compound was experienced over several months of study. As with any diazo compounds, caution should be exercised in handling of this compound and, especially, excessive heating should be avoided. As a precaution, it is recommended that all procedures using this compound should be carried out behind a blast shield.