Formaldehyde → 1-methyl-4-morpholin-4-ylmethyl-1H-pyrrole-2-carbaldehyde

HRID 1093969

Reaktionsgleichung

[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH3:7][N:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[CH:13]=[O:14].[CH2:15]=O>C(O)(=O)C.O>[CH3:7][N:8]1[CH:12]=[C:11]([CH2:15][N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)[CH:10]=[C:9]1[CH:13]=[O:14].[CH3:7][N:8]1[C:12]([CH2:15][N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[CH:11][CH:10]=[C:9]1[CH:13]=[O:14]

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

To a solution of morpholine (130 mmoles) in acetic acid (60 ml) at 0° C. there are added 1-methyl-1H-pyrrole-2-carbaldehyde (110 mmoles) and formaldehyde (110 mmoles) 37% in water. The reaction mixture is stirred for 16 hours at 50° C. After evaporation to dryness, about 100 ml of 25% aqueous sodium hydroxide solution are added. After extraction with DCM, the organic phase is washed with water and with saturated aqueous NaCl solution, dried over sodium sulphate, filtered and evaporated to dryness. The residue is purified by flash chromatography on silica gel (SiO2; gradient AcOEt/MeOH) to yield the title products 1-methyl-4-morpholin-4-ylmethyl-1H-pyrrole-2-carbaldehyde and 1-methyl-5-morpholin-4-ylmethyl-1H-pyrrole-2-carbaldehyde in a ratio of 1/5.

Aufarbeitung

customAfter evaporation to dryness, about 100 ml of 25% aqueous sodium hydroxide solution
additionare added
extractionAfter extraction with DCM
washthe organic phase is washed with water and with saturated aqueous NaCl solution
dry with materialdried over sodium sulphate
filtrationfiltered
customevaporated to dryness
customThe residue is purified by flash chromatography on silica gel (SiO2; gradient AcOEt/MeOH)

Quellen und Nachweise

ORD-Eintrag: ord-9649336304ea44fb80132f3e1b54a189
Quelldatensatz: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08133889B2

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