Methylenecyclobutane → Ethyl 5-oxa-6-azaspiro[3.4]oct-6-ene-7-carboxylate

HRID 1185940Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1185940
[CH2:1]=[C:2]1[CH2:5][CH2:4][CH2:3]1.Cl/[C:7](=[N:13]\[OH:14])/[C:8]([O:10][CH2:11][CH3:12])=[O:9].C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[CH2:11]([O:10][C:8]([C:7]1[CH2:1][C:2]2([CH2:5][CH2:4][CH2:3]2)[O:14][N:13]=1)=[O:9])[CH3:12]

Komponenten

5

Edukt 3

HCID 14262MethylenecyclobutaneHCID 516892Sodium Bicarbonate2×HCID 95760052-Chloro-2-hydroxyiminoacetic acid ethyl ester2×

Produkt 1

HCID 59611573Ethyl 5-oxa-6-azaspiro[3.4]oct-6-ene-7-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

To a solution of methylenecyclobutane (2 mL, 21.6 mmol) in ethyl acetate (125 mL) was added (Z)-ethyl 2-chloro-2-(hydroxyimino)acetate (6.55 g, 43.2 mmol) and solid sodium bicarbonate (16.3 g, 194 mmol). The reaction mixture was sealed and stirred at room temperature for 6 hours. More (Z)-ethyl 2-chloro-2-(hydroxyimino)acetate (4 g, 26.4 mmol) and sodium bicarbonate (8 g, 95.2 mmol) were added and the reaction was stirred at room temperature for an additional 12 hours. The reaction was diluted with ethyl acetate and washed successively with water and brine, dried (MgSO4) and concentrated to yield crude 5-oxa-6-aza-spiro[3.4]oct-6-ene-7-carboxylic acid ethyl ester, contaminated with (Z)-Ethyl 2-chloro-2-(hydroxyimino)acetate and related compounds.

Aufarbeitung

  1. customThe reaction mixture was sealed
  2. stirringthe reaction was stirred at room temperature for an additional 12 hours
  3. washwashed successively with water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-3a7590bf29734f35b508cbd37b5ce640
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08669234B2

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