Hydrochloric Acid → HCID 86594543, compound

HRID 1816429Notes

Reaction equation

HRID 1816429 reaction equation
C([O:3][C:4](=[O:32])/[CH:5]=[C:6](\[CH3:31])/[CH:7]=[CH:8]/[CH:9]=[C:10](/[C:15]1[C:24]([O:25][CH3:26])=[CH:23][C:22]2[C:21]([CH3:28])([CH3:27])[CH2:20][CH2:19][C:18]([CH3:30])([CH3:29])[C:17]=2[CH:16]=1)\[C:11]([F:14])([F:13])[F:12])C.[OH-].[Na+].Cl>CCO>[F:12][C:11]([F:13])([F:14])/[C:10](/[C:15]1[C:24]([O:25][CH3:26])=[CH:23][C:22]2[C:21]([CH3:27])([CH3:28])[CH2:20][CH2:19][C:18]([CH3:30])([CH3:29])[C:17]=2[CH:16]=1)=[CH:9]\[CH:8]=[CH:7]\[C:6](\[CH3:31])=[CH:5]\[C:4]([OH:32])=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86594540HCID 86594540, compound2×

Product 1

HCID 86594543HCID 86594543, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (2E,4E,6Z)-8,8,8-trifluoro-7-(3-methoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-3-methyl-octa-2,4,6-trienoic acid ethyl ester (Compound 1, 87 mg, 0.19 mmol) in EtOH (2 mL) was added 1M NaOH (0.68 mL). The mixture was heated to 60° C. for 2 h, was cooled to ambient temperature, acidified with 1M HCl, and extracted with EtOAc (×3). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (40% EtOAc-hexane) and HPLC (20% EtOAc-hexane) to give the title compound as a white solid (75 mg, 92%).

Workup

  1. temperaturewas cooled to ambient temperature
  2. extractionextracted with EtOAc (×3)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel (40% EtOAc-hexane) and HPLC (20% EtOAc-hexane)

Sources & evidence

ORD record
ord-caef956cd9b94afcb206abb9020c5f07
Source dataset
uspto-grants-2005_04
Patent number
US06884820B2

Reaction notes

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