Tetrahydrofuran → HCID 10496372, compound

HRID 466970Notes

Reaction equation

HRID 466970 reaction equation
C(Cl)(=O)[C:2](Cl)=[O:3].[C:7]([C:10]([S:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)C([O-])=O)([OH:9])=[O:8].O1CCC[CH2:31]1>CN(C=O)C>[CH3:21][C:18]1[CH:19]=[CH:20][C:15]2[CH2:14][C@H:10]([C:7]([O:9][CH3:31])=[O:8])[S:22][C@@H:23]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:2](=[O:3])[C:16]=2[CH:17]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 65578Oxalyl chlorideHCID 86746302HCID 86746302, compound

Product 1

HCID 10496372HCID 10496372, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

Oxalyl chloride (11.3 g) and DMF (3 drops) were successively added dropwise to a solution of 2-(carboxy)(phenyl)methylthio-3-(4-methylphenyl)propionate (25.5 g) in tetrahydrofuran (THF) (150 ml), followed by stirring for 1.5 hours at room temperature and concentrated under reduced pressure. The residual oil was dissolved in dichloromethane (50 ml). The solution was added dropwise to a suspension of aluminum chloride (AlCl3)(21.7 g) and dichloromethane (200 ml) with ice-cooling. The reaction mixture was stirred for 2 hours with ice-cooling and poured into ice-water. The dichloromethane layer was separated, washed with water, dried (MgSO4) and distilled off to give crystals of methyl trans-7-methyl-5-oxo-4-phenyl-1,2,4,5-tetrahydro-3-benzothiepine-2-carboxylate (7.2 g, 30%). Recrystallization from ethyl acetate-hexane gave colorless prisms.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residual oil was dissolved in dichloromethane (50 ml)
  3. additionThe solution was added dropwise to a suspension of aluminum chloride (AlCl3)(21.7 g) and dichloromethane (200 ml) with ice-
  4. temperaturecooling
  5. stirringThe reaction mixture was stirred for 2 hours with ice-
  6. temperaturecooling
  7. additionpoured into ice-water
  8. customThe dichloromethane layer was separated
  9. washwashed with water
  10. dry with materialdried (MgSO4)
  11. distillationdistilled off

Sources & evidence

ORD record
ord-41c298198ac9494892ce61116b5ee373
Source dataset
uspto-grants-1992_10
Patent number
US05158943

Reaction notes

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