Hydrochloric Acid → 1-(3-Tert-butyldiphenylsilyloxymethyl-2,4-dichlorophenyl)-2-cyanopyrrole

HRID 613607Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 613607
[Si:1]([O:18][CH2:19][C:20]1[C:21]([Cl:32])=[C:22]([N:27]2[CH:31]=[CH:30][CH:29]=[CH:28]2)[CH:23]=[CH:24][C:25]=1[Cl:26])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClS([N:37]=[C:38]=O)(=O)=O.CN(C)C=O.Cl>ClCCl>[Si:1]([O:18][CH2:19][C:20]1[C:21]([Cl:32])=[C:22]([N:27]2[CH:31]=[CH:30][CH:29]=[C:28]2[C:38]#[N:37])[CH:23]=[CH:24][C:25]=1[Cl:26])([C:14]([CH3:17])([CH3:15])[CH3:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 70918Chlorosulfonyl isocyanateHCID 183219091-(3-Tert-butyldiphenylsilyloxymethyl-2,4-dichlorophenyl)pyrrole

Produkt 1

HCID 183218191-(3-Tert-butyldiphenylsilyloxymethyl-2,4-dichlorophenyl)-2-cyanopyrrole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 1-[3-(tert-butyldiphenylsilyloxymethyl)-2,4-dichlorophenyl]pyrrole (1.20 g) in anhydrous dichloromethane (12 ml) was added a solution of chlorosulfonyl isocyanate (0.28 ml) in anhydrous dichloromethane (2.8 ml) dropwise in a dry ice-carbon tetrachloride bath. The mixture was stirred at the same temperature for 30 minutes and then at ambient temperature for additional 1 hour. Anhydrous dimethylformamide (0.4 ml) was added to this mixture dropwise in a dry ice-carbon tetrachloride bath. After stirring at the same temperature for 30 minutes and at ambient temperature for additional 1 hour, the reaction mixture was treated with 4N-hydrochloric acid under ice-water cooling for 30 minutes. The organic layer was isolated and the aqueous layer was extracted with chloroform twice. The combined organic phases were washed with saturated aqueous sodium hydrogen carbonate, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by a silica gel column chromatography eluted with n-hexane-ethyl acetate to give 1-[3-(tert-butyldiphenylsilyloxymethyl)-2,4-dichlorophenyl]-2-cyanopyrrole (930 mg) as a pale yellow oil.

Aufarbeitung

  1. waitat ambient temperature for additional 1 hour
  2. stirringAfter stirring at the same temperature for 30 minutes and at ambient temperature for additional 1 hour
  3. customThe organic layer was isolated
  4. extractionthe aqueous layer was extracted with chloroform twice
  5. washThe combined organic phases were washed with saturated aqueous sodium hydrogen carbonate
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo
  8. customThe residue was purified by a silica gel column chromatography
  9. washeluted with n-hexane-ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-7818cde904624f7894f1bd62e440256b
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US06008229

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