Hydrochloric Acid → HCID 5368428, compound

Participants

Reaction Steps

A solution of (E)-ethyl 5-phenylpent-2-enoate (732 mg) in dry toluene (5 ml) was cooled to −78° C. DIBAL-H (1 M in hexanes, 7.17 ml) was added dropwise and the mixture was stirred for 3 h. A second portion of DIBAL-H (1 M in hexanes, 0.717 ml) was added and stirring was continued for another 3 h. The mixture was allowed to warm-up to RT and hydrolyzed with 1 M aqueous HCl (5 ml). Additional 3M aqueous HCl was added until pH=1 and the aqueous layer was extracted with EtOAc (3×). The combined organic layer was washed with brine, dried over Na2SO4 and concentrated. The crude product was dissolved in dichloromethane (5 ml) and TEMPO (28.0 mg), potassium bromide (42.6 mg) and water (5 ml) were added. Aqueous sodium hypochlorite solution (13%, 1.642 ml) was added dropwise. The mixture was stirred at room temperature for 15 h. After phase separation the aqueous layer was extracted with CH2Cl2. The combined organic layer was washed with 1 M HCl, water and brine, dried over Na2SO4 and concentrated. The crude product was purified by flash column chromatography to yield a slightly orange oil.

Provenance & Evidence