Hydrochloric Acid → 4-(4-tert-Butyldiphenylsilyloxymethyl-phenyl)butyraldehyde

HRID 891

Reaktionsgleichung

Reaktionsgleichung von HRID 891
[Si:1]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][CH2:28][CH:29]2OCC[O:30]2)=[CH:22][CH:21]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C([O-])([O-])=O.[K+].[K+].N1C=CN=C1.C([Si](Cl)(C1C=CC=CC=1)C1C=CC=CC=1)(C)(C)C>C1COCC1>[Si:1]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][CH2:28][CH:29]=[O:30])=[CH:22][CH:21]=1)([C:14]([CH3:16])([CH3:17])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

7

Edukt 5

HCID 313Hydrochloric Acid2×HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 94078tert-ButyldiphenylchlorosilaneHCID 196941342-[3-(4-tert-Butyldiphenylsilyloxymethylphenyl)propyl]-[1,3]-dioxolane

Produkt 1

HCID 196941314-(4-tert-Butyldiphenylsilyloxymethyl-phenyl)butyraldehydeAusbeute 42,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 5.5 g (11.9 mmol) of the dioxolane 171 in 40 mL of THF at room temperature was added 40 mL of 4.0N HCl and the resulting solution was allowed to stir for 1 h. The mixture was neutralized with solid K2CO3, extracted with ethyl acetate and concentrated. The crude mixture was dissolved into 25 mL of CH2Cl2 to which was added 600 mg (8.8 mmol) of imidazole and 1.9 mL (7.3 mmol) of tert-butylchlorodiphenyl silane. The resulting mixture was allowed to stir overnight at room temperature and was then poured into 0.5N HCl and extracted with ethyl acetate. The organics were dried over MgSO4, filtered and concentrated. Flash chromatography (elution with 8% ethyl acetate in hexane) gave 2.12 g of the aldehyde 172 as an oil. 1H NMR consistent with the product.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. concentrationconcentrated
  3. dissolutionThe crude mixture was dissolved into 25 mL of CH2Cl2 to which
  4. stirringto stir overnight at room temperature
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organics were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. washFlash chromatography (elution with 8% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-991308a13d764cc0817ac696051b408e
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05723459

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