Ethanol → HCID 86759444, compound

HRID 1582097Notes

Reaction equation

HRID 1582097 reaction equation
[CH2:1]([O:3][C:4](=[O:31])/[CH:5]=[C:6](\[CH3:30])/[CH:7]=[CH:8]/[C:9](/[F:29])=[C:10](\[C:12]1[CH:13]=[C:14]([CH:26]([CH3:28])[CH3:27])[CH:15]=[C:16]2[C:21]=1[N:20]([CH2:22][CH3:23])[CH2:19][CH2:18][C:17]2([CH3:25])[CH3:24])/[CH3:11])[CH3:2].[CH2:32](O)C.[OH-].[Na+]>C1COCC1>[CH2:1]([O:3][C:4](=[O:31])/[CH:5]=[C:6](\[CH3:30])/[CH:7]=[CH:8]/[C:9](/[F:29])=[C:10](\[C:12]1[CH:13]=[C:14]([CH:26]([CH3:27])[CH3:28])[CH:15]=[C:16]2[C:21]=1[N:20]([CH2:22][CH2:23][CH3:32])[CH2:19][CH2:18][C:17]2([CH3:25])[CH3:24])/[CH3:11])[CH3:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 86759445HCID 86759445, compound2×

Product 1

HCID 86759444HCID 86759444, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of (2E,4E,6E)-7-(1-ethyl-6-isopropyl-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-8-yl)-6-fluoro-3-methyl-octa-2,4,6-trienoic acid ethyl ester (Compound 24, 117 mg, 2.74 mmol) and 5 ml of ethanol and 1 ml of THF was added 2 ml of 1 M NaOH(aq). The reaction was heated to 50° C. for 4 hours. The excess alcohol was removed by evaporation. The residue was neutralized with saturated NH4Cl to pH=7 then extracted with ethyl acetate (3×10 ml). The combined organic layers were washed with water, and brine, dried over Na2SO4 and concentrated to give the crude acid as a residue. This was purified by column chromatography (silica, first using 100% hexane, followed by 5:95 ethyl acetate:hexane, then 1:1 ethyl acetate:hexane) to yield a yellow oil. The resulting yellow oil was recrystallized from acetonitrile to produce the title compound as a yellow solid.

Workup

  1. customThe excess alcohol was removed by evaporation
  2. extractionthen extracted with ethyl acetate (3×10 ml)
  3. washThe combined organic layers were washed with water, and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto give the crude acid as a residue
  7. customThis was purified by column chromatography (silica
  8. customhexane, then 1:1 ethyl acetate:hexane) to yield a yellow oil
  9. customThe resulting yellow oil was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-d155d7d1454743b89f70ffaed1bc283f
Source dataset
uspto-grants-2004_05
Patent number
US06734193B1

Reaction notes

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