Methanol → HCID 18621282, compound

In a 250-mL r.b., a solution of 3-ethyl-1-pentyn-3-ol (11.5 g, 102 mmol) in pyridine (10.2 mL) was treated sequentially with Et3N (15.0 mL, 0.107 mol, 1.4 equiv), acetic anhydride (13.5 mL, 143 mmol, 1.4 equiv), and DMAP (1.25 g, 10.2 mmol, 10.0 mol % ). The reaction mixture was stirred at rt for 5 d, then treated with MeOH (5 mL) and stirred for 1 h. The mixture was partitioned between ether (100 mL) and water (100 mL), and the aqueous layer was extracted with ether (100 mL). The organic layers were washed sequentially with 2 N NaHSO4 and brine (50 mL), dried (MgSO4), filtered, and concentrated. Distillation under reduced pressure afforded 11.8 g (58.8%) 3-ethylpent-1-yn-3-yl acetate, a colorless oil, bp 38-39° C. @ 15 mm Hg. Data for 3-ethylpent-1-yn-3-yl acetate: 1H NMR (400 MHz, CDCl3) 2.54 (s, 1 H), 2.03 (s, 3H), 1.96-2.08 (m, 2H), 1.84-1.95 (m, 2H), 0.97 (t, J=7.4, 6H).

1. stirringstirred for 1 h
2. customThe mixture was partitioned between ether (100 mL) and water (100 mL)
3. extractionthe aqueous layer was extracted with ether (100 mL)
4. washThe organic layers were washed sequentially with 2 N NaHSO4 and brine (50 mL)
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated
8. distillationDistillation under reduced pressure

ORD record

ord-97d7d3a0706644c784b07146239a9175

Source dataset

uspto-grants-2003_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06534516B1