Dimethyl Sulfate → (1-Hydroxy-6-methoxy-4-methoxymethyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester

HRID 1798104Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1798104
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([OH:19])[CH:14]=[C:15]([CH2:16][O:17][CH3:18])[C:7]1=2)[CH3:2].[C:21]([O-])([O-])=O.[K+].[K+].COS(OC)(=O)=O>CC(C)=O.CCOC(C)=O>[CH2:1]([O:3][C:4](=[O:20])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([O:19][CH3:21])[CH:14]=[C:15]([CH2:16][O:17][CH3:18])[C:7]1=2)[CH3:2]

Komponenten

6

Edukt 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 58292640(1,6-Dihydroxy-4-methoxymethyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester

Produkt 1

HCID 58292600(1-Hydroxy-6-methoxy-4-methoxymethyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl esterAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of (1,6-dihydroxy-4-methoxymethyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester (0.18 g, 0.64 mmol) and K2CO3 (0.44 g, 3.2 mmol) in acetone was added Me2SO4 (0.16 g, 1.28 mmol). The mixture was stirred at room temperature for 16 hours then diluted with EtOAc. The organic extracts were washed with HCl (aq), dried and concentrated in vacuo. The residue was purified by silica gel flash column chromatography to give (1-hydroxy-6-methoxy-4-methoxymethyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester (0.060 g, 32%). 1H NMR (400 MHz, MeOD-d4) δ 7.08 (s, 1H), 6.99 (s, 1H), 5.62 (m, 1H), 5.50 (m, 2H), 4.08 (m, 2H), 3.80 (s, 3H), 3.37 (s, 3H), 3.12 (m, 1H), 2.17 (m, 1H), 1.20 (m, 3H).

Aufarbeitung

  1. washThe organic extracts were washed with HCl (aq)
  2. customdried
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-63963e4e8abf4321be4162590248d573
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08343944B2

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