Hydrogen Peroxide → HCID 13240723, compound

Participants

Reaction Conditions

Reaction Steps

A solution of the starting alkene 51 (1.5 g, 6.7 mmol) in THF (8 mL) was added dropwise to a cooled 1 M solution of BH3-THF (20.2 mL, 20.2 mmol). The reaction was stirred at 0° C. for 1 h and then allowed to stir for 2 h at room temperature. Excess diborane was decomposed by dropwise addition of water (10 mL). A 3 M solution of NaOH (10 mL) was then added, followed by dropwise addition of 30% H2O2 (10 mL). The reaction was stirred for 1 h at room temperature and K2CO3 (100 mg) was then added. The layers were then separated and the aqueous layer was extracted three times with CH2Cl2, the organic layers were pooled, dried over Na2SO4, then filtered and concentrated. After column chromatography (Rf=0.31, 50% hexanes/50% CH2Cl2) 52 was isolated as a yellow oil (1.2 g, 74%). 1H NMR (CDCl3) δ 3.49 (t, 2H), 1.53 (m, 1H), 1.41-1.22 (m, 28H); 13C NMR (CDCl3) δ 67.0, 39.5, 29.6, 27.5, 27.0, 26.7, 26.6, 26.5, 25.0.

Provenance & Evidence