Sodium hydride → 10-Dodecyn-1-ol

Temperature

70 °C

NaH (7.5 g, 60% oil dispersion, 326 mmol) was added portionwise to a stirring, 0° C. solution of dodec-3-yn-1-ol (10.0 g, 54.95 mmol; GF Smith) in ethylenediamine (40 mL). After 1 h, the temperature was raised to 70° C. After another 8 h, the reaction mixture was cooled to 0° C., carefully quenched with ice cold water (100 mL), and extracted with ether (3×60 mL). The combined ethereal extracts were washed with water (100 mL). The aqueous wash was back extracted with ether (3×60 mL). The combined organic extracts were concentrated in vacuo and the residue subjected to column chromatography using 10% EtOAc/hexanes afforded dodec-10-yn-1-ol (7.4 g, 74%) contaminated with 3-5% of other regioisomers. TLC: 30% EtOAc/hexane, Rf≈0.4; 1H NMR (300 MHz, CDCl3) δ 3.66 (t, 2H, J=7.3 Hz), 2.14-2.21 (m, 2H), 1.93 (t, J=1.9 Hz, 1H), 1.20-1.63 (m, 16H). Lit. ref: R. V. Novikov; A. A. Vasil'ev; I. A. Balova Russ. Chem. Bull., Internat. Ed. 2005: 54, 1043-1045.

1. waitAfter another 8 h
2. temperaturethe reaction mixture was cooled to 0° C.
3. customcarefully quenched with ice cold water (100 mL)
4. extractionextracted with ether (3×60 mL)
5. washThe combined ethereal extracts were washed with water (100 mL)
6. washThe aqueous wash
7. extractionwas back extracted with ether (3×60 mL)
8. concentrationThe combined organic extracts were concentrated in vacuo

ORD record

ord-6512514141624bfe92f8d896cf517e28

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09272991B2