p-Toluenesulfonic acid monohydrate → tert-butyl-dimethyl-[2-((S)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-ethoxy]-silane

HRID 1807058Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1807058
[C:1]([Si:5]([CH3:16])([CH3:15])[O:6][CH2:7][CH2:8][C@H:9]([OH:14])[C:10]([CH3:13])([OH:12])[CH3:11])([CH3:4])([CH3:3])[CH3:2].O.[C:18]1(C)[CH:23]=CC(S(O)(=O)=O)=C[CH:19]=1>COC(OC)(C)C>[C:1]([Si:5]([CH3:15])([CH3:16])[O:6][CH2:7][CH2:8][C@H:9]1[C:10]([CH3:11])([CH3:13])[O:12][C:18]([CH3:23])([CH3:19])[O:14]1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 71545770(S)-5-(tert-butyl-dimethyl-silanyloxy)-2-methyl-pentane-2,3-diol

Produkt 1

HCID 67299820tert-butyl-dimethyl-[2-((S)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-ethoxy]-silaneAusbeute 1.503,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 64952,2-DimethoxypropaneLösungsmittel

Versuchsvorschrift

Step E To a suspension of (S)-5-(tert-butyl-dimethyl-silanyloxy)-2-methyl-pentane-2,3-diol (6.8 g, 27 mmol) in 2,2-dimethoxypropane (35 mL) was added p-toluenesulfonic acid monohydrate (0.2 g). The reaction mixture was stirred at room temperature for 30 min. The mixture was partitioned between water and dichloromethane. The organic layer was separated, the aqueous layer was extracted with dichloromethane. The organic layers were combined, washed with water, brine, dried over MgSO4, and concentrated. The residue was purified by chromatography (EtOAc:hexanes=1:20) to give tert-butyl-dimethyl-[2-((S)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-ethoxy]-silane as a yellow oil (4.56 g, 58%).

Aufarbeitung

  1. customThe mixture was partitioned between water and dichloromethane
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with dichloromethane
  4. washwashed with water, brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography (EtOAc:hexanes=1:20)

Quellen und Nachweise

ORD-Eintrag
ord-330888b6efc94ac8ab53c204c54787cb
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08354444B2

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