Hydrogen Peroxide → HCID 13240723, compound

Temperature

0 °C

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.

1. stirringto stir for 2 h at room temperature
2. stirringThe reaction was stirred for 1 h at room temperature
3. customThe layers were then separated
4. extractionthe aqueous layer was extracted three times with CH2Cl2
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated

ORD record

ord-80a2ddb301aa44d1b1b31d10e9ce6247

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09266815B2