3-Butyn-1-OL → 157992-79-5

Stir a mixture of but-3-yn-1-ol (6.00 g; 85.60 mmol), tetrabutylammonium sulfate (2.07 g; 8.54 mmol) and sodium hydroxide (40% wt/wt; 150 mL) in dichloromethane (150 mL) at 0° C. Add tert-butyl bromoacetate (19.34 mL; 128.40 mmol) dropwise and stir the mixture for 2.5 hours at room temperature. Dilute the reaction mixture with dichloromethane (200 mL) and water (100 mL), separate the layers, and further extract the aqueous layer with dichloromethane (2×100 mL). Wash the combined organic layers with brine (100 mL), dry over anhydrous sodium sulfate, and concentrate to afford the crude title compound as a brown oil (11.93 g). Purify the oil by silica gel column chromatography, eluting with hexane:ethyl acetate (0% to 10% mixtures) to give the title compound (11.35 g; 72%) as a colorless oil. 1H NMR (CDCl3) δ 1.48 (s, 9H), 2.00 (m, 1H), 2.52 (m, 2H), 3.67 (m, 2H), 4.01 (bs, 2H).

1. customseparate the layers
2. extractionfurther extract the aqueous layer with dichloromethane (2×100 mL)
3. washWash the combined organic layers with brine (100 mL)
4. dry with materialdry over anhydrous sodium sulfate
5. concentrationconcentrate
6. customto afford the crude title compound as a brown oil (11.93 g)
7. customPurify the oil by silica gel column chromatography
8. washeluting with hexane

ORD record

ord-b686b19c26414e07a81856e1632a581b

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08969555B2