Dichloromethane → HCID 90282915, compound

To a stirred solution of 13 (2.40 g; 10.4 mmol) and triethylamine (2.92 ml; 2.12 g; 21.0 mmol) in methylene dichloride (50 ml) triethylsilyl trifluoromethanesulfonate (2.37 ml; 2.75 g; 10.4 mmol) was added dropwise at 0° C. After 15 min. N-bromosuccinimide (2.05 g; 11.5 mmol) was added and a cooling bath was removed. After 30 min. saturated aqueous solution of NH4Cl (10 ml) and water (50 ml) was added and the mixture was extracted with methylene dichloride (3×100 ml). Organic phase was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (hexane—5% ethyl acetate/hexane) to give 1.55 g (5.25 mmol; 50% yield) of 14. 1H NMR (400 MHz, CDCl3) δ 0.64 (6H, q, J=7.9 Hz), 0.97 (9H, t, J=7.9 Hz), 1.41 (6H, s), 4.44 (2H, s); 13C NMR (101 MHz, CDCl3) δ 6.5, 7.0, 27.8, 33.6, 80.4, 206.2; MS (EI) m/z 294 and 296 ([M−Et]+, 24 and 23), 187 (45), 173 (100); exact mass calculated for C9H18O2BrSi ([M−Et]+) 265.0254. found 265.0247.

1. customa cooling bath was removed
2. additionAfter 30 min. saturated aqueous solution of NH4Cl (10 ml) and water (50 ml) was added
3. extractionthe mixture was extracted with methylene dichloride (3×100 ml)
4. dry with materialOrganic phase was dried over anhydrous Na2SO4
5. concentrationconcentrated under reduced pressure
6. customThe residue was purified by column chromatography (hexane—5% ethyl acetate/hexane)

ORD record

ord-e9c3a47b931347088cec84b46eb9f02e

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09416102B2