Hydrochloric Acid → HCID 22406563, compound

HRID 440277Notes

Reaction equation

HRID 440277 reaction equation
[C:1]([O:5][C:6]([C:8]1[S:12][C:11]([C:13]([O:15]CC)=[O:14])=[C:10]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>O1CCOCC1>[C:1]([O:5][C:6]([C:8]1[S:12][C:11]([C:13]([OH:15])=[O:14])=[C:10]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 54105850HCID 54105850, compound

Product 1

HCID 22406563HCID 22406563, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of tert-butyl-3-tert-butoxy-2-ethyloxycarbonyl-5-thiophenecarboxylate (11.5 g, 35 mmol) in dioxane with NaOH (2N) (34.5 ml, 70 mmol) was heated for 1.45 hours at 50° C. The mixture was cooled to 0° C., neutralized with HCl (2N), and the solvent evaporated. The residue was triturated with a concentrated aqueous solution of Na2CO3 (400 ml) and ether (200 ml). The aqueous phase was recovered, cooled to 0° C., acidified with HCl (5N) and extracted with ether. After drying, concentration of the etheral phase, and purification by flash silica gel chromatography, the title compound was obtained (3.45 g).

Workup

  1. customthe solvent evaporated
  2. customThe residue was triturated with a concentrated aqueous solution of Na2CO3 (400 ml) and ether (200 ml)
  3. customThe aqueous phase was recovered
  4. temperaturecooled to 0° C.
  5. extractionextracted with ether
  6. customAfter drying
  7. customconcentration of the etheral phase, and purification by flash silica gel chromatography

Sources & evidence

ORD record
ord-becb827bde7f4141aae1bc1c3aefa318
Source dataset
uspto-grants-1996_05
Patent number
US05519015

Reaction notes

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