Dodecanoyl chloride → 4-Dodecoyloxymethyl-3-phenyl-2-triethylsilylfuran

HRID 2081345

Reaktionsgleichung

Reaktionsgleichung von HRID 2081345
[C:1]1([C:7]2[C:11]([CH2:12][OH:13])=[CH:10][O:9][C:8]=2[Si:14]([CH2:19][CH3:20])([CH2:17][CH3:18])[CH2:15][CH3:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:28](Cl)(=[O:40])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]>O1CCCC1>[C:28]([O:13][CH2:12][C:11]1[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[C:8]([Si:14]([CH2:17][CH3:18])([CH2:19][CH3:20])[CH2:15][CH3:16])[O:9][CH:10]=1)(=[O:40])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]

Komponenten

5

Edukt 3

HCID 8166Dodecanoyl chlorideHCID 8471TriethylamineHCID 150371503-Phenyl-2-triethylsilyl-4-furanmethanol2×

Produkt 1

HCID 150371514-Dodecoyloxymethyl-3-phenyl-2-triethylsilylfuran

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 3-phenyl-2-triethylsilyl-4-furanmethanol (345 mg, 1.20 mmol) and triethylamine (182 mg, 1.80 mmol) in tetrahydrofuran (Compound 64, 15 ml) at 0 degrees under argon was added lauroyl chloride (786 mg, 3.60 mmol). This solution was allowed to warm gradually to room temperature. After stirring an additional 2 hours the white precipitate was filtered off. The filtrate was taken up into ethyl ether, washed with saturated ammonium chloride, saturated sodium bicarbonate, H2O and brine. Evaporation of the dried (magnesium sulfate) extracts gave an oil which was purified by flash chromatography on silica using 2% ethyl ether/hexanes to give the title compound.

Aufarbeitung

  1. filtrationwas filtered off
  2. washwashed with saturated ammonium chloride, saturated sodium bicarbonate, H2O and brine
  3. customEvaporation of the
  4. dry with materialdried (magnesium sulfate)
  5. customextracts gave an oil which
  6. customwas purified by flash chromatography on silica using 2% ethyl ether/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-0fb7665a18f846109d90d9e4190a564a
Quelldatensatz
uspto-grants-1993_02
Patentnummer
US05183906

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