Acetic Acid → Methyl 3-(isopropyl-amino)-5-phenylthiophene-2-carboxylate

HRID 73168

Reaktionsgleichung

Reaktionsgleichung von HRID 73168
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][C:9]=1[NH2:10])=[O:4].CO[C:19]([CH3:21])=[CH2:20].CC(O)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>ClCCCl.CCOC(C)=O.O>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][C:9]=1[NH:10][CH:19]([CH3:21])[CH3:20])=[O:4]

Komponenten

9

Edukt 5

HCID 176Acetic AcidHCID 83002-MethoxypropeneHCID 516892Sodium BicarbonateHCID 700562Methyl 3-amino-5-phenylthiophene-2-carboxylateHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 11737447Methyl 3-(isopropyl-amino)-5-phenylthiophene-2-carboxylateAusbeute 96,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 111,2-DichloroethaneLösungsmittelHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred solution of 3-Amino-5-phenyl-thiophene-2-carboxylic acid methyl ester (1.82 g, 7.8 mmol) in 1,2-dichloroethane (40 mL) was added sequentially 2-methoxypropene (3.0 mL, 31.2 mmol), AcOH (1.8 mL, 31.2 mmol) and NaBH(OAc)3 (3.31 g, 15.6 mmol) and stirred for 2 hrs. It was then diluted with EtOAc and H2O. The aqueous solution was adjusted to pH=7 by adding NaHCO3. The aqueous phase was extracted with EtOAc, the combined extract was washed with brine and dried on MgSO4 and filtered. Purification on bond elute with hexane to 5% EtOAc-hexane furnished 3-Isopropylamino-5-phenyl-thiophene-2-carboxylic acid methyl ester (2.07 g, 96% yield). 1H NMR (CDCl3, 400 MHz): δ 7.62 (d, 2H), 7.40 (m, 3H), 6.91 (s, 1H), 3.84 (s, 3H), 3.71 (m, 1H), 1.35 (d, 6H).

Aufarbeitung

  1. extractionThe aqueous phase was extracted with EtOAc
  2. extractionthe combined extract
  3. washwas washed with brine
  4. customdried on MgSO4
  5. filtrationfiltered
  6. customPurification on bond
  7. washelute with hexane to 5% EtOAc-hexane

Quellen und Nachweise

ORD-Eintrag
ord-7eca7fdfe5a54abb85fa03b7ac19f993
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829030B2

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