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Ethylene Glycol → tert-butyl 9-(5-methyl-3-furyl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate

HRID 886914
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 886914
[CH:1]([C:3]1[O:7][CH:6]=[C:5]([C:8]2[C:18]3[O:17][CH2:16][CH2:15][N:14]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:13][C:12]=3[CH:11]=[CH:10][CH:9]=2)[CH:4]=1)=O.O.NN.C(O)CO.[OH-].[K+]>O.CO>[CH3:1][C:3]1[O:7][CH:6]=[C:5]([C:8]2[C:18]3[O:17][CH2:16][CH2:15][N:14]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:13][C:12]=3[CH:11]=[CH:10][CH:9]=2)[CH:4]=1
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Komponenten

7

Edukt 4

HCID 174Ethylene GlycolHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 86640603tert-butyl 9-(5-formyl-3-furyl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate

Produkt 1

HCID 68580313tert-butyl 9-(5-methyl-3-furyl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylateAusbeute 25 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of tert-butyl 9-(5-formyl-3-furyl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (300 mg, 0.874 mmol), hydrazine monohydrate (0.100 ml, 2.06 mmol), ethylene glycol (6 ml) and methanol (4 ml) was stirred at 70° C. for 10 min. After cooling to room temperature, potassium hydroxide (147 mg, 2.62 mmol) was added, and the mixture was stirred at 100° C. for 1 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to give the desired product (72.0 mg, 25.0%) as an oil.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. stirringthe mixture was stirred at 100° C. for 1 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-18a83b8e4a17432fb4bf1d4c2cf26502
Quelldatensatz
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08247403B2

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