Sodium borohydride → HCID 58292546, Verbindung

HRID 1798101Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1798101
[CH3:1][O:2][C:3](=[O:26])[CH2:4][CH2:5][C:6]([C:8]1[C:13]([B:14]2[O:18]C(C)(C)C(C)(C)[O:15]2)=[CH:12][C:11]([O:23][CH3:24])=[CH:10][C:9]=1[CH3:25])=O.[BH4-].[Na+].C(OB(O)O)C1C=CC=CC=1>CO>[CH3:1][O:2][C:3](=[O:26])[CH2:4][CH2:5][CH:6]1[O:18][B:14]([OH:15])[C:13]2[CH:12]=[C:11]([O:23][CH3:24])[CH:10]=[C:9]([CH3:25])[C:8]1=2

Komponenten

5

Edukt 3

HCID 4311764Sodium borohydrideHCID 17843933Benzyl dihydrogen borateHCID 58292569HCID 58292569, Verbindung

Produkt 1

HCID 58292546HCID 58292546, VerbindungAusbeute 69,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 4-[4-methoxy-2-methyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-4-oxo-butyric acid methyl ester (0.33 g, 0.87 mmol) in MeOH (3 mL) was added NaBH4 (0.073 g, 1.92 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 30 minutes, quenched with 6 N HCl and extracted with EtOAc. The organic extracts were dried and concentrated in vacuo. The residue was dissolved in CH3CN and treated with polymer-bounded benzyl boric acid (2 equiv) for 2 hours. The mixture was filtered, concentrated and purified by silica gel flash column chromatography to give 3-(1-hydroxy-6-methoxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-propionic acid methyl ester (0.160 g, 69%). 1H NMR (400 MHz, MeOD-d4) δ 6.98 (s, 1H), 6.80 (s, 1H), 5.25 (m, 1H), 3.80 (s, 3H), 3.60 (s, 3H), 2.50-2.30 (m, 6H), 1.77 (m, 1H).

Aufarbeitung

  1. customquenched with 6 N HCl
  2. extractionextracted with EtOAc
  3. customThe organic extracts were dried
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in CH3CN
  6. filtrationThe mixture was filtered
  7. concentrationconcentrated
  8. custompurified by silica gel flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-12bfadfe50c943edb9c57a205c81f5c6
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08343944B2

Notizen zur Reaktion

Wird geladen…