Lithium Hydroxide → 3-Iodo-1-(tetrahydro-pyran-2-yl)-1H-pyrazole-4-carboxylic acid

HRID 63296Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 63296
[I:1][C:2]1[C:6]([C:7]([O:9]CC)=[O:8])=[CH:5][N:4]([CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][O:13]2)[N:3]=1.[Li+].[OH-]>C1COCC1.CO.O>[I:1][C:2]1[C:6]([C:7]([OH:9])=[O:8])=[CH:5][N:4]([CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][O:13]2)[N:3]=1

Komponenten

6

Edukt 2

HCID 3939Lithium HydroxideHCID 58486565ethyl 3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-4-carboxylate

Produkt 1

HCID 904248953-Iodo-1-(tetrahydro-pyran-2-yl)-1H-pyrazole-4-carboxylic acidAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of ethyl 3-iodo-1-(oxan-2-yl)-1H-pyrazole-4-carboxylate (85 g, 242.75 mmol, 1.00 equiv) in THF (300 mL) and methanol (300 mL) was added a solution of LiOH (17.5 g, 730.69 mmol, 3.01 equiv) in water (400 mL). The resulting solution was stirred at room temperature overnight and then concentrated under vacuum to remove the organic solvent. The resulting solution was diluted with 400 mL of H2O and then acidified to pH 6.0 with 1M hydrochloric acid. The mixture was extracted with 3×800 mL of dichloromethane. The combined organic layers was washed with 3×1000 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum to give 75 g (96%) of 3-iodo-1-(oxan-2-yl)-1H-pyrazole-4-carboxylic acid as an off-white solid. LCMS (method D, ESI): RT=1.23 min, m/z=323.0 [M+H]+.

Aufarbeitung

  1. concentrationconcentrated under vacuum
  2. customto remove the organic solvent
  3. additionThe resulting solution was diluted with 400 mL of H2O
  4. extractionThe mixture was extracted with 3×800 mL of dichloromethane
  5. washThe combined organic layers was washed with 3×1000 mL of brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-0b555ffbf20044b5a808eaac13ee7560
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447079B2

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