Pyridine → 3-(2-Trimethylsilyl-4-furyl)propyl dodecanoate

HRID 345881Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 345881
N1C=CC=CC=1.[CH3:7][Si:8]([CH3:19])([CH3:18])[C:9]1[O:13][CH:12]=[C:11]([CH2:14][CH2:15][CH2:16][OH:17])[CH:10]=1.[C:20](Cl)(=[O:32])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]>O1CCCC1.CCOCC>[C:20]([O:17][CH2:16][CH2:15][CH2:14][C:11]1[CH:10]=[C:9]([Si:8]([CH3:7])([CH3:18])[CH3:19])[O:13][CH:12]=1)(=[O:32])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 8166Dodecanoyl chlorideHCID 150370913-(2-Trimethylsilyl-4-furyl)propan-1-ol

Produkt 1

HCID 150371273-(2-Trimethylsilyl-4-furyl)propyl dodecanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Pyridine (0.06 ml, 0.72 mmol) was added to a mixture of 3-(5-trimethylsilyl-3- furyl)propan-1-ol (from above) and lauroyl chloride (0.17 ml. 0.72 mmol) in tetrahydrofuran (4 ml) at room temperature. After 14 hours, the mixture was diluted with ether (10 ml) and washed successively with water, copper (II) sulphate and brine. Evaporation of the dried (magnesium sulphate) organic layers gave an oil, which was purified by preparative TLC (20×20 cm, 500μ silica plate; developed with 10% ethyl ether/petroleum ether). The title ester was obtained as a colorless oil.

Aufarbeitung

  1. washwashed successively with water, copper (II) sulphate and brine
  2. customEvaporation of the
  3. dry with materialdried (magnesium sulphate) organic layers
  4. customgave an oil, which
  5. customwas purified by preparative TLC (20×20 cm, 500μ silica plate; developed with 10% ethyl ether/petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-1b45da72dfdf4aee9c55053a04463be0
Quelldatensatz
uspto-grants-1991_10
Patentnummer
US05059611

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