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Acetic Acid → 2-(Methoxymethyl)-4-thiazolecarboxaldehyde

HRID 1174128
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1174128
[CH3:1][O:2][CH2:3][C:4]1[S:5][CH:6]=[C:7]([C:9](OCC)=[O:10])[N:8]=1.CC(C[AlH]CC(C)C)C.C(O)(=O)C.C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>ClCCl>[CH3:1][O:2][CH2:3][C:4]1[S:5][CH:6]=[C:7]([CH:9]=[O:10])[N:8]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 14487Diisobutylaluminum hydrideHCID 9855836Potassium sodium tartarateHCID 45117589Ethyl 2-(methoxymethyl)-1,3-thiazole-4-carboxylate

Produkt 1

HCID 451217662-(Methoxymethyl)-4-thiazolecarboxaldehydeAusbeute 99,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

A solution containing the product from Example 6C (7.4 g, 36.8 mmol) in dichloromethane (40 mL) was treated with DIBAL (73.6 mL, 1 M in dichloromethane) dropwise at −78° C. over 2 hours, stirred at −78° C. for 2 hours, treated with acetic acid (10 mL) at −78° C. and warmed to 25° C. A 10% solution of aqueous sodium potassium tartrate was added and the mixture was stirred vigorously for 1 hour. The reaction mixture was partitioned between chloroform and water. The organic phase was washed with brine, dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel eluting with 0-100% ethyl acetate/dichloromethane to give the title compound (5.78 g, 71% yield).

Aufarbeitung

  1. temperaturewarmed to 25° C
  2. stirringthe mixture was stirred vigorously for 1 hour
  3. customThe reaction mixture was partitioned between chloroform and water
  4. washThe organic phase was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was chromatographed on silica gel eluting with 0-100% ethyl acetate/dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-c757adf5ec8845cbb1f882e44d411b16
Quelldatensatz
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07834043B2

Notizen zur Reaktion

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