Hydrochloric Acid → Ethyl 3-oxo-3-(thiophen-3-yl)propanoate

HRID 2379173

Reaktionsgleichung

Reaktionsgleichung von HRID 2379173
C(NC1CCCCC1)(C)C.[Li]CCCC.[S:16]1[CH:20]=[CH:19][C:18]([C:21](Cl)=[O:22])=[CH:17]1.Cl.[CH3:25][CH2:26][O:27][C:28]([CH3:30])=[O:29]>C1COCC1.[Cl-].[Na+].O>[O:22]=[C:21]([C:18]1[CH:19]=[CH:20][S:16][CH:17]=1)[CH2:30][C:28]([O:27][CH2:26][CH3:25])=[O:29]

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 8857Ethyl Acetate2×HCID 62386CyclohexylisopropylamineHCID 27763773-Thenoyl chlorideHCID 178418339Butyllithium

Produkt 1

HCID 10535956Ethyl 3-oxo-3-(thiophen-3-yl)propanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To a solution of N-isopropylcyclohexylamine (5.64 g) in THF (80 mL) cooled to -78° C. under nitrogen was added nBuLi (25 mL, 1.6M in hexane) and the mixture was stirred for 30 min. EtOAc (1.95 mL) was added and after a further 30 min., 3-thiophene carbonyl chloride (from Step 1) dissolved in 3 mL THF was added. After 30 min., 1N HCl (75 mL) was added followed by brine and EtOAc. The organic layer was separated, dried and concentrated. Purification by column chromatography (5% EtOAc/hexane) afforded the title compound as an oil.

Aufarbeitung

  1. additionwas added
  2. waitAfter 30 min.
  3. customThe organic layer was separated
  4. customdried
  5. concentrationconcentrated
  6. customPurification by column chromatography (5% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-7d507e27a4b54b31a5a2d058be4c8a81
Quelldatensatz
uspto-grants-1994_11
Patentnummer
US05360815

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