Sodium Hydroxide → 5-chloro-4-(1-methyl-1H-pyrazol-5-yl)-2-furancarboxylic acid

HRID 1845539Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1845539
[Cl:1][C:2]1[O:6][C:5]([C:7]([O:9]C)=[O:8])=[CH:4][C:3]=1[C:11]1[N:15]([CH3:16])[N:14]=[CH:13][CH:12]=1.[OH-].[Na+]>O1CCCC1>[Cl:1][C:2]1[O:6][C:5]([C:7]([OH:9])=[O:8])=[CH:4][C:3]=1[C:11]1[N:15]([CH3:16])[N:14]=[CH:13][CH:12]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 57826770methyl 5-chloro-4-(1-methyl-1H-pyrazol-5-yl)-2-furancarboxylate

Produkt 1

HCID 578266115-chloro-4-(1-methyl-1H-pyrazol-5-yl)-2-furancarboxylic acidAusbeute 47,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of methyl 5-chloro-4-(1-methyl-1H-pyrazol-5-yl)-2-furancarboxylate (300 mg, 1.25 mmol) in 6N sodium hydroxide (4.16 ml, 24.93 mmol) and tetrahydrofuran (5.4 ml) was stirred at 70° C. in a sealed tube for 1 h. The resulting solution was cooled and then partitioned between H2O-DCM. The aqueous phase was adjusted to pH ˜4 and then washed several times with DCM. The combined organic fractions were dried over Na2SO4 and concentrated affording 5-chloro-4-(1-methyl-1H-pyrazol-5-yl)-2-furancarboxylic acid (267 mg, 0.59 mmol, 47% yield) as a white foam: LCMS (ES) m/e 265 (M+H)+.

Aufarbeitung

  1. temperatureThe resulting solution was cooled
  2. custompartitioned between H2O-DCM
  3. washwashed several times with DCM
  4. dry with materialThe combined organic fractions were dried over Na2SO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-387ac5892d1b474f841e88882d010bdc
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946278B2

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