Pyridine → 4-Dodecoyloxymethyl-2-trimethylsilylfuran

HRID 1090883Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1090883
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([Si:8]([CH3:11])([CH3:10])[CH3:9])[O:6][CH:7]=1.N1C=CC=CC=1.[C:18](Cl)(=[O:30])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>O1CCCC1>[C:18]([O:1][CH2:2][C:3]1[CH:4]=[C:5]([Si:8]([CH3:11])([CH3:10])[CH3:9])[O:6][CH:7]=1)(=[O:30])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 8166Dodecanoyl chlorideHCID 13333558(2-Trimethylsilyl-4-furyl)methanol

Produkt 1

HCID 150370464-Dodecoyloxymethyl-2-trimethylsilylfuran

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 4-hydroxymethyl-2-trimethylsilylfuran (0.288 g., 1.70 mmol) and pyridine (0.214 g., 2.55 mmol) in 30 ml dry tetrahydrofuran at 0 degrees was added lauroyl chloride (0.408 g., 1.86 mmol). This solution was allowed to warm to room temperature, stirred 30 minutes, and partitioned between ethyl ether and 5% sodium bicarbonate solution. The organic portion was washed with aqueous cupric sulfate solution, water, saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to a colorless oil. This material was purified by flash chromatography (silica, 5% ethyl ether/petroleum ether) to give the desired ester.

Aufarbeitung

  1. custompartitioned between ethyl ether and 5% sodium bicarbonate solution
  2. washThe organic portion was washed with aqueous cupric sulfate solution, water, saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to a colorless oil
  6. customThis material was purified by flash chromatography (silica, 5% ethyl ether/petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-17a65c8a8ffd4539b34283f25717d668
Quelldatensatz
uspto-grants-1992_01
Patentnummer
US05082954

Notizen zur Reaktion

Wird geladen…