Formic Acid → ethyl 2-formamido-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxylate

HRID 883180Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 883180
[NH2:1][C:2]1[S:6][C:5]2[CH2:7][CH2:8][CH2:9][C:4]=2[C:3]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11].[C:15]([O-])(=[O:17])C.[NH4+].C(O)=O>O>[CH:15]([NH:1][C:2]1[S:6][C:5]2[CH2:7][CH2:8][CH2:9][C:4]=2[C:3]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:17]

Komponenten

5

Edukt 3

HCID 284Formic AcidHCID 264105ethyl 2-amino-4H,5H,6H-cyclopenta[b]thiophene-3-carboxylateHCID 517165Ammonium Acetate

Produkt 1

HCID 759951ethyl 2-formamido-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxylateAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of compound 2g [Compound of Formula 2 wherein R1=COOEt, R2, R3=(CH2)3] (10.0 g, 0.046 mol), ammonium acetate (3.64 g, 0.060 mol) and formic acid (35.74 mL, 0.946 mol) was stirred at 130-135° C. for 8 h. It was then cooled to room temperature and diluted with water (150 mL), extracted with ethyl acetate (3×100 mL), dried over Na2SO4, concentrated and purified by column chromatography to give pure compound of Formula (3g); 10.66 g; Yield: 97%; 1H NMR (200 MHz, CDCl3+DMSO-d6): δ 0.1.33 (t, J=8 Hz, 3H), 2.25-2.43 (m, 2H), 2.74-2.89 (m, 4H), 4.26 (q, J=8 Hz, 2H), 8.48 (s, 1H) 11.16 (bs, 1H).

Aufarbeitung

  1. extractionextracted with ethyl acetate (3×100 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. custompurified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8557d059286c43c1baee15a495105537
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08236840B2

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