Thionyl Chloride → 2-(1,4-Dioxaspiro[4.5]dec-7-en-8-yl)pyridine

HRID 1173180Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1173180
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1(O)[CH2:16][CH2:15][C:10]2([O:14][CH2:13][CH2:12][O:11]2)[CH2:9][CH2:8]1.O=S(Cl)Cl>N1C=CC=CC=1>[O:14]1[C:10]2([CH2:15][CH2:16][C:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)=[CH:8][CH2:9]2)[O:11][CH2:12][CH2:13]1

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 21187637HCID 21187637, Verbindung

Produkt 1

HCID 211876502-(1,4-Dioxaspiro[4.5]dec-7-en-8-yl)pyridineAusbeute 83,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

The ketal (2 g, 8.5 mmol) obtained from step A, Example 7 was dissolved in pyridine (40 mL) and the solution was cooled in an ice bath. To it was added SOCl2 (3.1 mL, 42.5 mmol). The solution was allowed to warm to room temperature and stirring was continued overnight. The reaction was quenched by addition of ice and then water. The resulting solution was extracted with EtOAc three times. The combined EtOAc layer was dried over MgSO4 and concentrated. Flash chromatography on silica gel eluting with 0 to 55% EtOAc/hexanes provided 1.54 g of the title compound. MS calculated (M+H)+ 218, found 218.

Aufarbeitung

  1. temperaturethe solution was cooled in an ice bath
  2. customThe reaction was quenched by addition of ice
  3. extractionThe resulting solution was extracted with EtOAc three times
  4. dry with materialThe combined EtOAc layer was dried over MgSO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-6d5106fe54914368b1289b0161d41259
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07834021B2

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