Hydrochloric Acid → HCID 19096301, compound

HRID 486717Notes

Reaction equation

HRID 486717 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:10][CH2:9][CH:8]([C:11]([O:13]CC)=[O:12])[S:7]1)=[O:5])[CH3:2].[OH-].[K+].C(OCC)C.Cl>C(O)C.O>[C:11]([CH:8]1[CH2:9][CH2:10][CH:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[S:7]1)([OH:13])=[O:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 14797Potassium HydroxideHCID 14993186HCID 14993186, compound

Product 1

HCID 19096301HCID 19096301, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

To a solution of 2,5-diethoxycarbonyltetrahydrothiophene (2.4 g) in ethanol (10 ml), potassium hydroxide (0.64 g) dissolved in ethanol (10 ml) was added dropwise and the mixture was stirred for 1 hour at room temperature. To the reaction mixture, diethyl ether and water were added. Aqueous layer was acidified with 2N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated in vacuo to give 1.6 g (78%) of 2-carboxy-5-ethoxycarbonyltetrahydrothiophene.

Workup

  1. additionwas added dropwise
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6c17c3e197b14e76bff124ed188d0b42
Source dataset
uspto-grants-1994_03
Patent number
US05292767

Reaction notes

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