Hydrochloric Acid → HCID 65405396, compound

Temperature

-5 °C

A solution of malonic acid monoethyl ester (3.8 g, 29 mmol) in THF (80 ml) was cooled to −78° C. n-BuLi (36 ml, 58 mmol, 1.6 M in hexane) was added dropwise so that the temperature of the reaction mixture at the end the addition was −5° C. After 5 min. stirring at −5° C., reaction mixture was cooled to −65° C. and treated with a solution of (RS)-1,2,3,4-tetrahydro-naphthalene-2-carbonyl chloride (3.2 g, 16.5 mmol) in THF. Mixture was stirred for 10 min. at −65° C. and then added to a stirring mixture containing Et2O (200 ml) and 1N HCl (100 ml). Aqueous phase was extracted with Et2O (2×150 ml). Combined organic phases were washed successively with a saturated solution of NaHCO3 (100 ml) and NaCl (100 ml), dried over Na2SO4 and concentrated to provide (RS)-3-oxo-3-(1,2,3,4-tetrahydro-naphthalen-2-yl)-propionic acid ethyl ester (3.8 g, 93%) as a light brown oil, MS: m/e=246 (M+).

1. additionwas added dropwise so that the temperature of the reaction mixture at the end
2. additionthe addition
3. customwas −5° C
4. customreaction mixture
5. temperaturewas cooled to −65° C.
6. stirringMixture was stirred for 10 min. at −65° C.
7. additionadded to a stirring mixture
8. extractionAqueous phase was extracted with Et2O (2×150 ml)
9. washCombined organic phases were washed successively with a saturated solution of NaHCO3 (100 ml) and NaCl (100 ml)
10. dry with materialdried over Na2SO4
11. concentrationconcentrated

ORD record

ord-62201c187017419b91a70b5c7808a7d1

Source dataset

uspto-grants-2002_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06440995B1