Hydrochloric Acid → HCID 13891056, compound

Participants

Reaction Steps

A 2 g (0.01 mole) portion of the compound from Example 26 was dissolved in THF (50 mL) and treated at 0°-5° C. with 37.5 mL of an 0.8 M solution of isopentyl magnesium bromide in THF. The reaction was stirred for 2 hours at room temperature and then poured into ice water which contained 6.5 mL of 6 N HCl. The mixture was extracted with methylene chloride. Evaporation of the dried methylene chloride solution gave a quantitative yield of the Grignard adduct. This material was dissolved in 300 mL of acetone and treated by dropwise addition with Jones solution until the orange color persisted. The chromium salts were filtered and the filtrate was evaporated. The residue was diluted with ether and the resulting solution was washed successively with aqueous NaHCO3 and brine solution. After drying over MgSO4, the solvent was evaporated to give 1.7 g (66%) of product as an oil. NMR (300 MHz, CDCl3, ppm): 0.86-0.96 (m, 12H), 2.41 (M, 2H), 2.67 (m, 2H), 3.5 (m, 1H), 4.15 (m, 1H).

Provenance & Evidence