Sodium Hydroxide → HCID 18319512, compound

HRID 1699381Notes

Reaction equation

HRID 1699381 reaction equation
[CH3:1][S:2][C:3]1[C:4]([O:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:5]([CH:11]=[CH:12][CH:13]=1)[C:6]([O:8]CC)=O.[OH-].[Na+]>C(O)C.CN(C)C=O>[CH3:1][S:2][C:3]1[C:4]2[O:14][CH2:15][CH2:16][CH:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:6](=[O:8])[C:5]=2[CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 18319529HCID 18319529, compound

Product 1

HCID 18319512HCID 18319512, compoundYield 79.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 3-methylthio-2-(3-ethoxycarbonylpropoxy)benzoate (3.83 g) in a mixture of ethanol (34 μl) and N,N-dimethylformamide (40 ml) was added 60% sodium hydroxide (1.03 mg) at 5° C. After the mixture was allowed to stir at room temperature for 15.5 hours, it was poured into ice-water and extracted with ethyl acetate (x 3). The combined extracts were washed with water (x 2) and brine, dried over magnesium sulfate, and evaporated in vacuo. The crude product was purified by column chromatography on silica gel using a mixture of n-hexane and ethyl acetate (20:1) to give ethyl 9-methylthio-5-oxo-2,3,4,5-tetrahydro-1-benzoxepin-4-carboxylate (2.61 g, colorless crystals).

Workup

  1. extractionextracted with ethyl acetate (x 3)
  2. washThe combined extracts were washed with water (x 2) and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe crude product was purified by column chromatography on silica gel using
  6. additiona mixture of n-hexane and ethyl acetate (20:1)

Sources & evidence

ORD record
ord-651a2788e8e643cc9813a4c291e950e5
Source dataset
uspto-grants-2002_02
Patent number
US06346527B1

Reaction notes

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