Water → 2-((S)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-ethanol

HRID 1807059Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1807059
C([Si](C)(C)[O:6][CH2:7][CH2:8][C@H:9]1[C:13]([CH3:15])([CH3:14])[O:12][C:11]([CH3:17])([CH3:16])[O:10]1)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1>[CH3:16][C:11]1([CH3:17])[O:10][C@@H:9]([CH2:8][CH2:7][OH:6])[C:13]([CH3:15])([CH3:14])[O:12]1

Komponenten

5

Edukt 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 67299820tert-butyl-dimethyl-[2-((S)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-ethoxy]-silane

Produkt 1

HCID 672994832-((S)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-ethanolAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Step F To the solution of tert-butyl-dimethyl-[2-((S)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-ethoxy]-silane (4.56 g, 15.8 mmol) in tetrahydrofuran (20 mL) at 0° C. was added a solution of tetrabutylammonium fluoride (1 M, 20 mL, 20 mmol). The reaction mixture was stirred at room temperature for 1 h. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was separated, washed with saturated aqueous NaHCO3 solution, brine, dried over MgSO4, and concentrated to give 2-((S)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-ethanol as a yellow oil (2.7 g, 100%).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with saturated aqueous NaHCO3 solution, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-fa11ba77150a4d23a335711a9a18d4df
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08354444B2

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