Ammonium Chloride → methyl 5-(hydroxymethyl)-1-methyl-1H-pyrrole-2-carboxylate

HRID 1009474Notes

Reaction equation

[CH:1]([C:3]1[N:7]([CH3:8])[C:6]([C:9]([O:11][CH3:12])=[O:10])=[CH:5][CH:4]=1)=[O:2].[BH4-].[Na+].[Cl-].[NH4+]>C1COCC1>[OH:2][CH2:1][C:3]1[N:7]([CH3:8])[C:6]([C:9]([O:11][CH3:12])=[O:10])=[CH:5][CH:4]=1

Participants

Conditions

Temperature: -20 °C

Procedure

670 mg of methyl 5-formyl-1-methyl-1H-pyrrole-2-carboxylate was dissolved in 10.0 mL of THF, and 303 mg of sodium borohydride was added thereto at −20° C., followed by stirring at −20° C. for 30 minutes, and then at 0° C. for further 1 hour. To the reaction liquid was added an aqueous saturated ammonium chloride solution, followed by extraction with ethyl acetate. The organic layer was washed with an aqueous saturated sodium hydrogen carbonate solution and brine, and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain 592 mg of methyl 5-(hydroxymethyl)-1-methyl-1H-pyrrole-2-carboxylate.

Workup

customat −20° C.
waitat 0° C. for further 1 hour
customTo the reaction liquid
extractionfollowed by extraction with ethyl acetate
washThe organic layer was washed with an aqueous saturated sodium hydrogen carbonate solution and brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-1083655ced704d539f6868bc191c9cc1
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07973078B2

Reaction notes

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