3-(1-Hydroxytridecyl)-5-trimethylsilylfuran → 4-[1-(Dodecanoyloxy)tridecyl]2-trimethylsilylfuran

HRID 1109872Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1109872
[C:1]([Li])([CH3:4])([CH3:3])C.[OH:6][CH:7]([C:20]1[CH:21]=[C:22]([Si:25]([CH3:28])([CH3:27])[CH3:26])[O:23][CH:24]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]>CCCCC.O1CCCC1>[C:7]([O:6][CH:7]([C:20]1[CH:21]=[C:22]([Si:25]([CH3:28])([CH3:27])[CH3:26])[O:23][CH:24]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])(=[O:6])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:3][CH2:1][CH3:4]

Komponenten

5

Edukt 2

HCID 156632683-(1-Hydroxytridecyl)-5-trimethylsilylfuranHCID 178418306HCID 178418306, Verbindung

Produkt 1

HCID 150370684-[1-(Dodecanoyloxy)tridecyl]2-trimethylsilylfuran

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8003PentaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

tert-Butyl lithium (a 1.7 M solution in pentane; 0.21 ml, 0.36 mmol) was added dropwise to a solution of 4-(1-hydroxytridecyl)-2-trimethylsilylfuran (124.5 mg, 0.37 mmol) in tetrahydrofuran (5 ml) at 0 degrees under argon. After 5 minutes, the cooling bath was removed and lauroyl chloride (88 microliter) was added. The mixture was stirred at room temperature for 16 hours and quenched with water. Extraction (ethyl ether) and evaporation of the dried (magnesium sulphate) extracts gave an oil, which was purified by preparative TLC (20×20 cm, 1000u silica plate; developed with 5% ethyl ether/hexane). The title ester was obtained as a colorless oil.

Aufarbeitung

  1. customthe cooling bath was removed
  2. additionlauroyl chloride (88 microliter) was added
  3. customquenched with water
  4. extractionExtraction (ethyl ether) and evaporation of the
  5. dry with materialdried (magnesium sulphate)
  6. customextracts gave an oil, which
  7. customwas purified by preparative TLC (20×20 cm, 1000u silica plate; developed with 5% ethyl ether/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-5e57403ab92943feb4aedf7b43e90035
Quelldatensatz
uspto-grants-1994_06
Patentnummer
US05322953

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