8-Methoxy-8-oxooctanoic acid → Methyl 8-hydroxyoctanoate

HRID 649732

Reaktionsgleichung

Reaktionsgleichung von HRID 649732
[CH3:1][O:2][C:3](=[O:13])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10](O)=[O:11].B.C1COCC1>O1CCCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:13])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][OH:11]

Komponenten

5

Edukt 2

HCID 5541918-Methoxy-8-oxooctanoic acidHCID 2723981Borane;tetrahydrofuran

Produkt 1

HCID 554055Methyl 8-hydroxyoctanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of suberic acid monomethyl ester (1.5 g, 7.97 mmol, 1.0 equiv.) in tetrahydrofuran (THF) (32.0 mL, .25M) at −20° C. was treated dropwise with BH3.THF (IM solution in THF, 7.97 mL, 7.97 mmol, 1.0 equiv.). The reaction mixture was stirred overnight and was subsequently allowed to reach room temperature. The reaction mixture was then diluted with ethyl acetate (100 mL) and quenched with methanol (10 mL) and 10% HCl (10 mL). Extraction with NaHCO3 (1×20 mL), water (2×10 mL), and brine (1×10 mL), afforded methyl-8-hydroxy-octanoate

Aufarbeitung

  1. customto reach room temperature
  2. customquenched with methanol (10 mL) and 10% HCl (10 mL)
  3. extractionExtraction with NaHCO3 (1×20 mL), water (2×10 mL), and brine (1×10 mL)

Quellen und Nachweise

ORD-Eintrag
ord-0759684ec69045f69084e061b180e743
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06271015B1

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