Hydrochloric Acid → HCID 22609582, compound

HRID 2306792Notes

Reaction equation

HRID 2306792 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH:9]=[C:8]([C:15]#[C:16][C:17]([O:19]CC)=[O:18])[CH2:7][CH2:6]2.[OH-].[K+].Cl>CO.O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH:9]=[C:8]([C:15]#[C:16][C:17]([OH:19])=[O:18])[CH2:7][CH2:6]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 22609540HCID 22609540, compound

Product 1

HCID 22609582HCID 22609582, compoundYield 103.4%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Added to a solution of 65.2 mg (0.23 mmol) of ethyl 3-(3,4-dihydro-6,7-dimethoxy-2-naphthyl)-2-propynoate synthesized by the process described in Referential Example 13 in methanol-tetrahydrofuran (1:1; 1 ml) was 0.5 ml (2.5 mmol) of a 5N aqueous solution of potassium hydroxide, and the mixture was stirred for 30 minutes at room temperature. A saturated saline solution and 0.25 ml (3.0 mmol) of concentrated hydrochloric acid were added to the reaction mixture to conduct extraction with chloroform. An organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resultant concentrated residue was purified by column chromatography on silica gel to obtain 61.4 mg (quantitative) of 3-(3,4-dihydro-6,7-dimethoxy-2-naphthyl)-2-propynoic acid as a colorless amorphous powder.

Workup

  1. customsynthesized by the process
  2. extractionextraction with chloroform
  3. dry with materialAn organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resultant concentrated residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-4498ef0c28f34f93af8cbe32b569256c
Source dataset
uspto-grants-2004_12
Patent number
US06828316B2

Reaction notes

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