Methyl chloroacetate → Methyl 2-(3-nitropyridin-4-yl)acetate

3-Nitropyridine (5.00 g, 40.3 mmol) and methyl chloroacetate (7.30 g, 67.3 mmol) were dissolved in THF (50 mL) and added drop-wise to a slurry of KOtBu (18.1 g, 161 mmol) in THF (50 mL) at 0° C. The reaction mixture was stirred at RT for 1 h, cooled to 0° C. and quenched with sat aq NH4Cl (100 mL). The THF was removed in vacuo and the reaction mixture was diluted with DCM (75 mL). The aq fraction was extracted with DCM (3×40 mL) and the combined organic fractions were washed with brine (100 mL), dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography to give the title compound as a dark brown oil (3.94 g, 50%). LCMS (ES+): 196.9 [MH]+.

1. temperaturecooled to 0° C.
2. customquenched with sat aq NH4Cl (100 mL)
3. customThe THF was removed in vacuo
4. additionthe reaction mixture was diluted with DCM (75 mL)
5. extractionThe aq fraction was extracted with DCM (3×40 mL)
6. washthe combined organic fractions were washed with brine (100 mL)
7. dry with materialdried (MgSO4)
8. concentrationconcentrated in vacuo
9. customThe residue was purified by column chromatography

ORDレコード

ord-61ab4aae59fb4a96b60c9fd3652048e4

出典データセット

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09150574B2