Hydrochloric Acid → HCID 22609582, compound

HRID 1250966Notes

Reaction equation

HRID 1250966 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-dd290dbfd66741739bb14e4ec46180fe
Source dataset
uspto-grants-2002_01
Patent number
US06340682B1

Reaction notes

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