Hydrochloric Acid → HCID 19745039, compound

HRID 2254309Notes

Reaction equation

HRID 2254309 reaction equation
[CH2:1]=[C:2]([CH2:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:3]([OH:5])=[O:4].C(N(CC)CC)C.[SH:20][C:21]1[S:22][CH:23]=[CH:24][CH:25]=1.Cl>C1COCC1>[S:22]1[CH:23]=[CH:24][CH:25]=[C:21]1[S:20][CH2:1][CH:2]([CH2:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:3]([OH:5])=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 5226742-ThiophenethiolHCID 197450382-Methylene-4-ethoxycarbonylbutyric acid

Product 1

HCID 19745039HCID 19745039, compoundYield 53.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under N2, a mixture of 2-methylene-4-ethoxycarbonylbutyric acid (17 g, 0.09 mol), triethylamine (4.3 g, 0.04 mol) in THF (120 ml) and 2-mercaptothiophene (11 g, 0.095 mol) was heated at reflux. After 24 hours the reaction mixture was cooled to room temperature and poured into 3N HCl (400 ml). The aqueous layer was extracted with EtOAc (3×) and the combined organic extracts were backwashed with saturated NaCl, dried, filtered and concentrated to dryness. The residue was chromatographed on a Still column and the product eluted with 15% CH3OH-CHCl3 saturated with NH3 to yield 14 g of 1 wherein R1, R2, R3 and R4 are each H.

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. extractionThe aqueous layer was extracted with EtOAc (3×)
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe residue was chromatographed on a Still column
  8. washthe product eluted with 15% CH3OH-CHCl3 saturated with NH3

Sources & evidence

ORD record
ord-da13e842121c4199a6add2c21d92fa20
Source dataset
uspto-grants-1993_08
Patent number
US05235059

Reaction notes

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