Dimethylformamide → HCID 25140998, Verbindung

HRID 1511221

Reaktionsgleichung

Reaktionsgleichung von HRID 1511221
[CH:1](N(CC)C(C)C)(C)C.[CH3:10][O:11][C:12]1[CH:13]=[C:14]([OH:19])[CH:15]=[C:16]([OH:18])[CH:17]=1.[CH3:20][O:21][CH2:22]Cl.CN(C)[CH:26]=[O:27]>>[CH3:10][O:11][C:12]1[CH:17]=[C:16]([O:18][CH2:20][O:21][CH3:22])[CH:15]=[C:14]([O:19][CH2:1][O:27][CH3:26])[CH:13]=1

Komponenten

5

Edukt 4

HCID 6228DimethylformamideHCID 7864Chloromethyl Methyl EtherHCID 71648FlamenolHCID 81531Diisopropylethylamine

Produkt 1

HCID 25140998HCID 25140998, VerbindungAusbeute 43 %

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

N,N-diisopropylethylamine (3.15 mL, 18.1 mmol) was added to 5-methoxybenzene-1,3-diol (634 mg, 4.52 mmol) in anhydrous N,N-dimethylformamide (12.6 mL) over 5 minutes at room temperature. After 30 minutes, the solution was cooled to 0° C., methoxy methylchloride (3.02 mL, 18.1 mmol) was added, and the solution was warmed to room temperature over 12 hours. The reaction was quenched by the addition of saturated aqueous NaHCO3 at 0° C. and extracted with EtOAc (3×10 mL). Combined organic fractions were washed with saturated aqueous NaCl, dried (Na2SO4), filtered, and concentrated. The residue was purified via column chromatography (SiO2, 6:1→4:1 Hexane:EtOAc) to afford 8 as a yellow amorphous solid (441 mg, 43%): 1H NMR (CDCl3, 500 MHz) 6.29 (t, J=2.2 Hz, 1H), 6.21 (d, J=2.2 Hz, 2H), 5.07 (s, 4H), 3.69 (s, 3H), 3.40 (s, 6H); 13C NMR (CDCl3, 125 MHz) 161.394, 159.0 (2C), 97.2, 96.2 (2C), 94.5 (2C), 56.1, 55.4 (2C); IR (film) νmax 2997, 2955, 2903, 2827, 1601, 1475, 1400, 1215, 1194, 1146, 1032, 991, 924, 829, 685 cm−1; HRMS (ESI+) m/z: [M+Na]+ calcd for C11H16O5, 251.0895. found, 251.0910.

Aufarbeitung

  1. temperaturethe solution was warmed to room temperature over 12 hours
  2. customThe reaction was quenched by the addition of saturated aqueous NaHCO3 at 0° C.
  3. extractionextracted with EtOAc (3×10 mL)
  4. washCombined organic fractions were washed with saturated aqueous NaCl
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified via column chromatography (SiO2, 6:1→4:1 Hexane:EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-aa294d0dd797463190c5e57e39a29496
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08212011B2

Verknüpfte Notizen

Wird geladen…