Sodium Hydroxide → 5-Mercapto-2,2-dimethylpentanoic acid ethyl ester

To a solution of 5-bromo-2,2-dimethylpentanoic acid ethyl ester (2.41 g, 10 mmol) in ethyl alcohol (5 mL) was added thiourea (0.77 g, 10 mmol) and the mixture was refluxed for 3 h under a nitrogen atmosphere. A solution of sodium hydroxide (0.62 g, 15 mmol) in deionized water (2.5 mL) was added and stirring was continued for another 2 h at reflux temperature. The mixture was cooled to rt and the ethanol was distilled off under reduced pressure. Diethyl ether (20 mL) was added and the layers were separated. The organic phase was washed with saturated sodium chloride solution (5 mL), dried over sodium sulfate, filtered, and concentrated in vacuo to give 5-mercapto-2,2-dimethylpentanoic acid ethyl ester (1.41 g, 74%) as a yellow oil. 1H NMR (300 MHz, CDCl3/TMS): d (ppm): 4.12 (q, J=7.0 Hz, 2H), 2.57-2.43 (m, 2H), 1.69-1.45 (t, 4H), 1.25 (t, J=7.0 Hz, 3H), 1.17 (s, 7H). 13C NMR(75 MHz, CDCl3/TMS): d (ppm): 177.55, 41.0, 39.24, 25.07, 24.90, 14.18.

1. temperaturethe mixture was refluxed for 3 h under a nitrogen atmosphere
2. temperatureat reflux temperature
3. distillationthe ethanol was distilled off under reduced pressure
4. additionDiethyl ether (20 mL) was added
5. customthe layers were separated
6. washThe organic phase was washed with saturated sodium chloride solution (5 mL)
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated in vacuo

ORD record

ord-878b5f2ef79b40218137b48bdd1a0bd1

Source dataset

uspto-grants-2004_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06703422B2