Hydrochloric Acid → (2E,4E,6E)-7-(3-Ethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-6-fluoro-3-methylnona-2,4,6-trienoic acid

HRID 1744909Notes

Reaction equation

HRID 1744909 reaction equation
[CH2:1]([O:3][C:4]1[C:5](/[C:18](/[CH2:31][CH3:32])=[C:19](/[F:30])\[CH:20]=[CH:21]\[C:22](\[CH3:29])=[CH:23]\[C:24]([O:26]CC)=[O:25])=[CH:6][C:7]2[C:8]([CH3:17])([CH3:16])[CH2:9][CH2:10][C:11]([CH3:15])([CH3:14])[C:12]=2[CH:13]=1)[CH3:2].[OH-].[K+].Cl>C(O)C>[CH2:1]([O:3][C:4]1[C:5](/[C:18](/[CH2:31][CH3:32])=[C:19](/[F:30])\[CH:20]=[CH:21]\[C:22](\[CH3:29])=[CH:23]\[C:24]([OH:26])=[O:25])=[CH:6][C:7]2[C:8]([CH3:16])([CH3:17])[CH2:9][CH2:10][C:11]([CH3:14])([CH3:15])[C:12]=2[CH:13]=1)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 86593751Ethyl (2E,4E,6E)-7-(3-ethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-6-fluoro-3-methylnona-2,4,6-trienoate2×

Product 1

HCID 9888036(2E,4E,6E)-7-(3-Ethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-6-fluoro-3-methylnona-2,4,6-trienoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of ethyl (2E,4E,6E)-7-(3-ethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-6-fluoro-3-methylnona-2,4,6-trienoate (Compound 1, 3.55 g, 8.02 mmol) in ethanol (60 mL) was treated with 2 N aqueous potassium hydroxide (20 mL), and the solution was stirred at 60° C. overnight. The solution was cooled to room temperature, and acidified with 1 N HCl, and the products were extracted three times with ethyl acetate. The combined organic layers were washed with water, brine and dried over magnesium sulfate. The solution was filtered through a sintered glass funnel containing a bed of silica gel about 1 inch thick using ethyl acetate as the eluent. The solvent was removed in vacuo, and the residue was recrystalized form acetonitrile to give the title compound.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. extractionthe products were extracted three times with ethyl acetate
  3. washThe combined organic layers were washed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe solution was filtered through a sintered glass funnel
  6. additioncontaining a bed of silica gel about 1 inch
  7. customThe solvent was removed in vacuo
  8. customthe residue was recrystalized form acetonitrile

Sources & evidence

ORD record
ord-bc30eac34f6f4987943ee07fed5e38c2
Source dataset
uspto-grants-2006_03
Patent number
US07019034B2

Reaction notes

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