1-Butanol, 4-chloro-, 1-acetate → HCID 118324351, compound

Temperature

80 °C

To a 500 mL flask was added 5.0 g (33 mmol, 1.0 eq) of 4-chlorobutylacetate and dissolved in 100 mL of DMF. Next 2.6 g (40 mmol, 1.2 eq) of sodium azide was added by a glass pipette. A water condenser was placed onto the flask and the reaction heated to 80° C. for 16 hr with stirring. The reaction was then cooled to room temperature and quenched with 300 mL of water to dissolve the sodium salts. The aqueous solution was extracted with diethyl ether 3×100 mL. The organic layers were combined and dried with MgSO4. The solution was filtered and concentrated under vacuum with no external heat, resulting in 4-azido-1-butylacetate (4.22), which was carried onto the next step without further purification; 1H NMR (CDCl3, 300 MHz): δ: 4.04 (t, J=6.0 Hz, 2H), 3.27 (t, J=6.2 Hz, 2H), 2.00 (s, 3H), 1.76-1.52 (m, 4H). 13C NMR (75 MHz, CDCl3) δ: 170.82, 63.55, 50.84, 25.73, 25.39, 20.73. 81% yield, clear oil.

1. customA water condenser was placed onto the flask
2. temperatureThe reaction was then cooled to room temperature
3. customquenched with 300 mL of water
4. dissolutionto dissolve the sodium salts
5. extractionThe aqueous solution was extracted with diethyl ether 3×100 mL
6. dry with materialdried with MgSO4
7. filtrationThe solution was filtered
8. concentrationconcentrated under vacuum with no external heat
9. customresulting in 4-azido-1-butylacetate (4.22)
10. customwhich was carried onto the next step without further purification

ORD record

ord-b5930feab76e47b994d4bd63c842336b

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09376385B2