3,3-Dimethylbutane-1,2-diol → Ethyl 5-(4-(tert-butyl)-1,3-dioxolan-2-yl)-4-methylisoxazole-3-carboxylate

HRID 1478201

Reaktionsgleichung

Reaktionsgleichung von HRID 1478201
[CH:1]([C:3]1[O:7][N:6]=[C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:4]=1[CH3:13])=[O:2].[CH3:14][C:15]([CH3:21])([CH3:20])[CH:16](O)[CH2:17][OH:18]>C1(C)C=CC=CC=1>[C:15]([CH:16]1[CH2:17][O:18][CH:1]([C:3]2[O:7][N:6]=[C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:4]=2[CH3:13])[O:2]1)([CH3:21])([CH3:20])[CH3:14]

Komponenten

4

Edukt 2

HCID 1010773,3-Dimethylbutane-1,2-diolHCID 118511140Ethyl 5-formyl-4-methylisoxazole-3-carboxylate2×

Produkt 1

HCID 118511117Ethyl 5-(4-(tert-butyl)-1,3-dioxolan-2-yl)-4-methylisoxazole-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a solution of ethyl 5-formyl-4-methylisoxazole-3-carboxylate (Intermediate C) (50 mg, 0.273 mmol) in toluene (0.5 mL) was added 3,3-dimethylbutane-1,2-diol (32.3 mg, 0.273 mmol) and the mixture was heated at 110° C. for 4.5 hours. The resulting mixture was partitioned between EtOAc and water and the organic layer was dried over MgSO4, filtered and the solvent removed under reduced pressure. The crude material was adsorbed onto silica and purification by chromatography eluting with 0-100% EtOAc in iso-hexane afforded the title compound;

Aufarbeitung

  1. customThe resulting mixture was partitioned between EtOAc and water
  2. dry with materialthe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. customthe solvent removed under reduced pressure
  5. customThe crude material was adsorbed onto silica and purification by chromatography
  6. washeluting with 0-100% EtOAc in iso-hexane

Quellen und Nachweise

ORD-Eintrag
ord-5b80751ffd1a4ad08adacccadddd3e24
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09403810B2

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