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

HRID 21570

Reaction equation

HRID 21570 reaction equation
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]

Participants

8

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-3fafb40f159e43c99b50e87fa2e6886b
Source dataset
uspto-grants-1995_06
Patent number
US05424320

Linked notes

Loading…