1-Bromodecane → HCID 21895375, compound

Into a dry 250 mL three-necked round-bottomed flask equipped with magnetic stirring bar and dropping funnel was placed 8 g (0.07 mol) of fresh N-vinylformamide potassium salt and 200 mL of anhydrous THF. 1-Bromodecane, 16.1 g (0.07 mol) was added to the reaction mixture dropwise at 10° C. over 30 minutes. When addition was complete, the reaction was allowed to stir overnight at ambient temperature. The reaction mixture was concentrated under reduced pressure to remove most of the solvent and diluted with 100 mL of water. The organic layer was extracted with diethyl ether. The combined organic layers were washed twice with water and dried over anhydrous magnesium sulfate. The product was recovered after concentration in vacuum and purification by chromatography on silica (diethyl ether/petroleum ether (v/v=2:8). Yield: 13.2 g (89%). IR (NaCl, v: cm−1):1702 (—NHC(═O)H); 1631 (C═C); 1H-NMR (CDCl3, δ: ppm): 8.43, 8.27 (2s, 1H, —C(═O)H); 7.37–7.28, 6.73–6.65 (m, 1H, H2C═CH—); 4.78–4.67 (m, 1H, HaHbC═CH—); 4.58–4.55 (d, 1H, HaHbC═CH—); 3.72–3.56 (t, 2H, —NCH2CH2—); 1.76–1.62 (m, 2H, —NCH2CH2(CH2)7CH3); 1.44–1.28 (m, 14H, —NCH2CH2(CH2)7CH3); 1.04–1.00 (t, 3H, —NCH2CH2(CH2)7CH3).

1. customInto a dry 250 mL three-necked round-bottomed flask equipped with magnetic stirring bar
2. additionWhen addition
3. concentrationThe reaction mixture was concentrated under reduced pressure
4. customto remove most of the solvent
5. additiondiluted with 100 mL of water
6. extractionThe organic layer was extracted with diethyl ether
7. washThe combined organic layers were washed twice with water
8. dry with materialdried over anhydrous magnesium sulfate
9. customThe product was recovered
10. concentrationafter concentration
11. customin vacuum and purification by chromatography on silica (diethyl ether/petroleum ether (v/v=2:8)

ORD record

ord-ad7fabb0e30644408467e8392644b4fa

Source dataset

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07135598B2