2,2-Dimethoxypropane → HCID 86756341, Verbindung

HRID 567897Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 567897
[NH2:1][C:2]1[S:3][C:4]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].CO[C:21](OC)([CH3:23])[CH3:22].[BH4-].[Na+]>C1(C)C=CC=CC=1.C(O)C.O.CC1C=CC(S(O)(=O)=O)=CC=1>[CH3:22][CH:21]([NH:1][C:2]1[S:3][C:4]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:23]

Komponenten

8

Edukt 3

HCID 64952,2-DimethoxypropaneHCID 3792137ethyl 2-amino-5-benzylthiophene-3-carboxylateHCID 4311764Sodium borohydride

Produkt 1

HCID 86756341HCID 86756341, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 6101p-Toluenesulfonic acidKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of 2-amino-5-(phenylmethyl)thiophene-3-carboxylic acid, ethyl ester (2.61 g) and 4-methylbenzenesulfonic acid (30mg) in dry toluene (50 ml) was added 2,2-dimethoxypropane. The solution was heated to reflux for 5 hours and then allowed to cool to ambient temperature. A solution of sodium borohydride (800 mg) in ethanol (100 ml) was added to the solution and the mixture was stirred at room temperature under nitrogen for 24 hours. The mixture was diluted with water and then extracted thrice with ethyl acetate. The combined organic extracts were washed with brine and then dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure to give an oil. The residue was purified by column chromatography over silica, eluting with diethyl ether:isohexane (1:19) to give the subtitle compound (550 mg).

Aufarbeitung

  1. temperatureThe solution was heated
  2. temperatureto reflux for 5 hours
  3. extractionextracted thrice with ethyl acetate
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customto give an oil
  9. customThe residue was purified by column chromatography over silica
  10. washeluting with diethyl ether:isohexane (1:19)

Quellen und Nachweise

ORD-Eintrag
ord-12e33d0101b04236bb0405962bdc5ff5
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06180635B2

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