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Sodium Thiosulfate → 3-(6-t-Butyldimethylsilyloxymethylnaphthalen-2-yl)propionaldehyde

HRID 348736
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 348736
[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH:16]=[C:15]([CH2:20][CH2:21][CH2:22][OH:23])[CH:14]=[CH:13]2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>ClCCl>[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH:16]=[C:15]([CH2:20][CH2:21][CH:22]=[O:23])[CH:14]=[CH:13]2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 230791693-(6-t-Butyldimethylsilyloxymethylnaphthalen-2-yl)propan-1-ol

Produkt 1

HCID 230791943-(6-t-Butyldimethylsilyloxymethylnaphthalen-2-yl)propionaldehydeAusbeute 83,6 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The compound (1.18 g) obtained in Example 121-6 was dissolved in anhydrous dichloromethane (25 ml) and added with Dess-Martin periodinane (1.82 g), followed by stirring at room temperature for 2 hours. After completion of the reaction, a sodium thiosulfate aqueous solution and a saturated aqueous sodium bicarbonate solution were added to the solution, and the whole was stirred. Then, the solution was extracted with chloroform and the extract was then washed with an aqueous mixture solution of a sodium thiosulfate aqueous solution and a saturated sodium bicarbonate aqueous solution. Then, the organic layer was dried with anhydrous sodium sulfate and the solvent was distilled off. The residue was purified through silica gel column chromatography (hexane/ethyl acetate), thereby obtaining the subject compound (981 mg) as a white solid.

Aufarbeitung

  1. customAfter completion of the reaction
  2. stirringthe whole was stirred
  3. extractionThen, the solution was extracted with chloroform
  4. washthe extract was then washed with an aqueous mixture solution of a sodium thiosulfate aqueous solution
  5. dry with materialThen, the organic layer was dried with anhydrous sodium sulfate
  6. distillationthe solvent was distilled off
  7. customThe residue was purified through silica gel column chromatography (hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-70af4eed4917440d9197a820f48ee9cb
Quelldatensatz
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07176227B2

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