Sodium Hydroxide → (3-Chloroisoquinolin-8-yl)methanol

HRID 920247Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 920247
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[C:12](O)=[O:13].B.C1COCC1.[OH-].[Na+]>C1COCC1.CCOC(C)=O>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[CH2:12][OH:13]

Komponenten

6

Edukt 3

HCID 14798Sodium HydroxideHCID 2723981Borane;tetrahydrofuranHCID 895248833-Chloroisoquinoline-8-carboxylic acid

Produkt 1

HCID 89524955(3-Chloroisoquinolin-8-yl)methanol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 3-chloroisoquinoline-8-carboxylic acid (0.5 g, 1.803 mmol) in THF (18.03 ml) at 0° C. was treated with BH3.THF (5.41 ml, 5.41 mmol). After stirring for 2 hours at 0° C., 1N NaOH was added. The reaction was stirred for 30 minutes then diluted with EtOAc and the layers were separated. Aqueous layer was washed with EtOAc three times. All combined organic layers were washed with brine, then dried with sodium sulfate. Filtered and concentrated in vacuo. Purified by silica gel chromatography (0-100% EtOAc in hexane) to yield (3-chloroisoquinolin-8-yl)methanol.

Aufarbeitung

  1. stirringThe reaction was stirred for 30 minutes
  2. customthe layers were separated
  3. washAqueous layer was washed with EtOAc three times
  4. washAll combined organic layers were washed with brine
  5. dry with materialdried with sodium sulfate
  6. filtrationFiltered
  7. concentrationconcentrated in vacuo
  8. customPurified by silica gel chromatography (0-100% EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-58fbf893efed4b78941cd3312d112788
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09273040B2

Notizen zur Reaktion

Wird geladen…