Water → 3,4,5-Triacetoxy-6-(2-vinyl-thiophen-3-yloxy)-tetrahydropyran-2-ylmethyl acetate

HRID 1445329

Reaktionsgleichung

Reaktionsgleichung von HRID 1445329
[C:1]([O:4][CH2:5][CH:6]1[CH:11]([O:12][C:13](=[O:15])[CH3:14])[CH:10]([O:16][C:17](=[O:19])[CH3:18])[CH:9]([O:20][C:21](=[O:23])[CH3:22])[CH:8]([O:24][C:25]2[CH:29]=[CH:28][S:27][C:26]=2[CH:30]=O)[O:7]1)(=[O:3])[CH3:2].[C:32](=O)([O-])[O-].[K+].[K+].O>O1CCOCC1.[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]([O:4][CH2:5][CH:6]1[CH:11]([O:12][C:13](=[O:15])[CH3:14])[CH:10]([O:16][C:17](=[O:19])[CH3:18])[CH:9]([O:20][C:21](=[O:23])[CH3:22])[CH:8]([O:24][C:25]2[CH:29]=[CH:28][S:27][C:26]=2[CH:30]=[CH2:32])[O:7]1)(=[O:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 219612443,4,5-Triacetoxy-6-(2-formyl-thiophen-3-yloxy)-tetrahydropyran-2-ylmethyl acetate

Produkt 1

HCID 219612203,4,5-Triacetoxy-6-(2-vinyl-thiophen-3-yloxy)-tetrahydropyran-2-ylmethyl acetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74505Methyltriphenyliphosphonium bromideKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

3.30 g of 3,4,5-triacetoxy-6-(2-formyl-thiophen-3-yloxy)-tetrahydropyran-2-ylmethyl actate were dissolved in 60 ml of dioxane. 6.43 g of methyltriphenylphosphonium bromide, 5.37 g of potassium carbonate and 0.25 ml of water were added, and the solution was refluxed for 4 h. The solution was concentrated and purified by column filtration. 2.89 g of the product with the molecular weight: 456.47 (C20H24O10S), MS (ESI): 479.10 (M+Na+); 474.10 (M+NH4+) were obtained.

Aufarbeitung

  1. temperaturethe solution was refluxed for 4 h
  2. concentrationThe solution was concentrated
  3. filtrationpurified by column filtration
  4. custom474.10 (M+NH4+) were obtained

Quellen und Nachweise

ORD-Eintrag
ord-167895b9b96c43f397478376529b1d5a
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07666848B2

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