Ethyl Acetate → 2-{1-[(Benzyloxy)methyl]cyclobutyl}ethanethioamide

HRID 1180766Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1180766
[CH2:1]([O:8][CH2:9][C:10]1([CH2:14][C:15]#[N:16])[CH2:13][CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([S:19]P([O-])(OCC)=S)C.C(OCC)(=O)C>O1CCCC1.O>[CH2:1]([O:8][CH2:9][C:10]1([CH2:14][C:15](=[S:19])[NH2:16])[CH2:11][CH2:12][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 8857Ethyl AcetateHCID 11148614{1-[(Benzyloxy)methyl]cyclobutyl}acetonitrileHCID 53249491Diethyldithiophosphate

Produkt 1

HCID 112651762-{1-[(Benzyloxy)methyl]cyclobutyl}ethanethioamideAusbeute 71,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 9.7 g (45 mmol) of {1-[(benzyloxy)methyl]cyclobutyl}acetonitrile in 100 mL of tetrahydrofuran and 10 mL of water was added 15.13 mL (90.2 mmol) of diethyldithiophosphate and the contents heated at reflux for 16 h. Ethyl acetate and water were added, and the layers separated. The organic phase was dried using magnesium sulfate and concentrated under vacuum to afford the crude product, which was purified by silica gel chromatography using ethyl acetate:hexane (2:8) as the eluent to afford 8.0 g (71%) of 2-{1-[(benzyloxy)methyl]cyclobutyl}ethanethioamide as a colorless oil. 1H NMR (300 MHz, CDCl3) δ 8.00 (br s, 2H), 7.39-7.30 (m, 5H), 4.59 (s, 2H), 3.58 (s, 2H), 3.09 (s, 2H), 2.14-1.87 (m, 6H).

Aufarbeitung

  1. temperaturethe contents heated
  2. temperatureat reflux for 16 h
  3. customthe layers separated
  4. customThe organic phase was dried
  5. concentrationconcentrated under vacuum
  6. customto afford the crude product, which
  7. customwas purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-2e7c945452a44b5dbe56d6ed99610ada
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07282512B2

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