Sodium Thiosulfate → 2-(4-(2-(tert-Butyldimethylsilyloxy)ethyl)phenyl)acetaldehyde

HRID 1689202Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1689202
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[C:23]([Si:27]([CH3:41])([CH3:40])[O:28][CH2:29][CH2:30][C:31]1[CH:36]=[CH:35][C:34]([CH2:37][CH2:38][OH:39])=[CH:33][CH:32]=1)([CH3:26])([CH3:25])[CH3:24].S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>ClCCl.C(OCC)(=O)C>[Si:27]([O:28][CH2:29][CH2:30][C:31]1[CH:32]=[CH:33][C:34]([CH2:37][CH:38]=[O:39])=[CH:35][CH:36]=1)([C:23]([CH3:25])([CH3:24])[CH3:26])([CH3:41])[CH3:40]

Komponenten

7

Edukt 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 233774542-{4-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-phenyl}-ethanol

Produkt 1

HCID 579893082-(4-(2-(tert-Butyldimethylsilyloxy)ethyl)phenyl)acetaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Dess-Martin periodinane (0.38 g) was added to a solution of 2-(4-(2-(tert-butyldimethylsilyloxy)ethyl)phenyl)ethanol (example 5, step b) (0.21 g) in dichloromethane (5 mL) and the resulting mixture stirred for 30 min. A mixture of saturated sodium thiosulphate solution (5 mL), saturated sodium bicarbonate solution (5 mL) and ethyl acetate (25 mL) were added and the resulting mixture stirred for 10 min. The organic phase was separated and washed with saturated sodium bicarbonate solution (2×10 mL) and brine (10 mL), then dried over sodium sulphate, filtered and evaporated to give the subtitled compound as a clear oil which was used immediately. Yield 0.20 g.

Aufarbeitung

  1. additionwere added
  2. stirringthe resulting mixture stirred for 10 min
  3. customThe organic phase was separated
  4. washwashed with saturated sodium bicarbonate solution (2×10 mL) and brine (10 mL)
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-1fb6a9376ba945caa185e5be731d3846
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148373B2

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