Hydrogen Peroxide → methyl 3-chloro-5-(2-hydroxyethyl)-1H-pyrrole-2-carboxylate

A stirred solution of methyl 3-chloro-5-ethenyl-1H-pyrrole-2-carboxylate (0.100 g, 0.539 mmol) in THF (5 mL) was treated with 9-BBN (5.39 mL, 2.15 mmol). The reaction was stirred at RT overnight. The reaction mixture was treated with 1 mL of 1N NaOH and 1 mL of 30% H2O2 and stirred. The reaction mixture was partitioned between EtOAc and a solution of sodium metabisulfite. The organic layer was separated, dried over MgSO4 and evaporated to a residue. The residue was taken up in 1N LiOH (1 mL), MeOH (1 mL) and THF (1 mL) and heated until the acid was formed as seen on TLC. The reaction was evaporated, acidified and extracted with EtOAc. The organic layer was separated and dried over MgSO4 to afford methyl 3-chloro-5-(2-hydroxyethyl)-1H-pyrrole-2-carboxylate (0.028 g, 27%) as a solid. LCMS: m/z=188.0 (M−1).

1. stirringstirred
2. customThe reaction mixture was partitioned between EtOAc
3. customThe organic layer was separated
4. dry with materialdried over MgSO4
5. customevaporated to a residue
6. temperatureMeOH (1 mL) and THF (1 mL) and heated until the acid
7. customwas formed
8. customThe reaction was evaporated
9. extractionextracted with EtOAc
10. customThe organic layer was separated
11. dry with materialdried over MgSO4

ORD record

ord-72bf66197ccd43d692f6a04245428c6b

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08304419B2