Methyl 2-bromopropionate → HCID 86749253, compound

Temperature

-30 °C

A three-neck, round-bottomed flask, equipped with a dropping funnel and septum, was charged with 1.76 g (10 mmol) of 8-methoxy-2-tetralone and 20 mL of THF under a nitrogen atmosphere. The solution was cooled to -30° C. and 7.5 mL (11 mmol) of LDA (1.5M in cyclohexane) was added dropwise. The solution was stirred for 30 minutes and warmed to 0° C. To this solution, 1.3 mL (12 mmol) of methyl bromopropionate was added. The solution was stirred at room temperature for two hours. The reaction was quenched with 3 N HCl until pH of the mixture was <3. THF was removed in vacuo and the concentrate was extracted with methylene chloride (2×500 mL). The organic layer was washed with brine, dried (MgSO4), filtered and concentrated in vacuo to give a yellow oil. This oil was purified by liquid chromatography on 400 g silica gel 60 (230-400 m), eluting with hexane-acetone (4:1), and collecting 40 mL fractions. Fractions homogeneous by TLC were combined and concentrated in vacuo to give 1.63 g (63%) of the title compound as a yellow oil.

1. customA three-neck, round-bottomed flask, equipped with a dropping funnel
2. temperaturewarmed to 0° C
3. stirringThe solution was stirred at room temperature for two hours
4. customThe reaction was quenched with 3 N HCl until pH of the mixture
5. customTHF was removed in vacuo
6. extractionthe concentrate was extracted with methylene chloride (2×500 mL)
7. washThe organic layer was washed with brine
8. dry with materialdried (MgSO4)
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customto give a yellow oil
12. customThis oil was purified by liquid chromatography on 400 g silica gel 60 (230-400 m)
13. washeluting with hexane-acetone (4:1)
14. customcollecting 40 mL fractions
15. concentrationconcentrated in vacuo

ORD record

ord-20a20d43bbb645ba899a6f6208fdea3a

Source dataset

uspto-grants-1996_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05491236