Hydrochloric Acid → HCID 86698278, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of sodium selenide (5.35 g, 42.49 mmol) in DMF (43 mL) was added a solution of methyl 3-chloro-4,4-dimethylpent-2-enoate (7.5 g, 42.49 mmol) in DMF (10 mL) at rt for 5 min and stirred the mixture at 60-70° C. for 2 h. Then chloroacetonitrile (2.785 mL, 42.49 mmol) was added dropwise to the reaction mixture and again stirred at 60-70° C. for 2 h. Then, a solution of sodium methoxide (2.29 g, 42.49 mmol) in dry methanol (26 mL) was added dropwise and stirring was continued for 1 h at the same temperature. The reaction mixture was poured into ice cold water and acidified with dil. HCl. The solution was extracted with chloroform (3×200 mL) and the combined chloroform layer was washed with water, brine and dried over sodium sulfate. The solution was filtered and evaporated the solvent. The residue was chromatographed over silica gel column using hexane-EtoAc (80:20) as eluents to give the product as a red color oil (7.5 g, 77%). 1H NMR (400 MHz, CDCl3): δ 6.76 (1H, s), 1.35 (9H, s); LC-MS (negative ion mode): m/z 226, 228 (M−H)−.

Provenance & Evidence