Hydrochloric Acid → HCID 22490962, compound

HRID 2180585Notes

Reaction equation

HRID 2180585 reaction equation
[CH2:1]([O:3][C:4]1[C:5](/[C:16](/[CH3:29])=[C:17](/[F:28])\[CH:18]=[CH:19]\[C:20](\[CH3:27])=[CH:21]\[C:22]([O:24]CC)=[O:23])=[CH:6][C:7]2[CH:8]=[CH:9][CH2:10][C:11]([CH3:15])([CH3:14])[C:12]=2[CH:13]=1)[CH3:2].[OH-].[Na+].Cl>C(O)C.C1COCC1>[CH2:1]([O:3][C:4]1[C:5](/[C:16](/[CH3:29])=[C:17](/[F:28])\[CH:18]=[CH:19]\[C:20](\[CH3:27])=[CH:21]\[C:22]([OH:24])=[O:23])=[CH:6][C:7]2[CH:8]=[CH:9][CH2:10][C:11]([CH3:15])([CH3:14])[C:12]=2[CH:13]=1)[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86597847HCID 86597847, compound

Product 1

HCID 22490962HCID 22490962, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of ethyl (2E,4E,6E)-7-(3-ethoxy-5,5-dimethyl-5,6-dihydro-naphthalen-2-yl)-6-fluoro-3-methyl-octa-2,4,6-trienoate (Compound A-67, 4.0 mg, 0.01 mmol) in ethanol (0.2 mL) and THF (1 mL) was added 1M NaOH (0.05 mL, 0.05 mmol). The mixture was heated to 60° C. for 5 h and was cooled to room temperature, acidified with 1M HCl, extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, 10% ethyl acetate in hexanes) to give the title compound as a white solid.

Workup

  1. temperaturewas cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography (silica gel, 10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-84817d9bf3184fa9acd147f272029882
Source dataset
uspto-grants-2005_05
Patent number
US06887896B1

Reaction notes

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