Sodium Hydroxide → (2E,4E,6E)-6-Fluoro-7-(4-isopropyl-7-methoxy-2,2-dimethyl-2H-chromen-6-yl)-3-methyl-octa-2,4,6-trienoic acid

HRID 2180524Notes

Reaction equation

HRID 2180524 reaction equation
[F:1]/[C:2](=[C:13](/[C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][C:24]=1[O:25][CH3:26])[O:21][C:20]([CH3:28])([CH3:27])[CH:19]=[C:18]2[CH:29]([CH3:31])[CH3:30])\[CH3:14])/[CH:3]=[CH:4]/[C:5](/[CH3:12])=[CH:6]/[C:7]([O:9]CC)=[O:8].[OH-].[Na+]>C(O)C.C1COCC1>[F:1]/[C:2](=[C:13](/[C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][C:24]=1[O:25][CH3:26])[O:21][C:20]([CH3:28])([CH3:27])[CH:19]=[C:18]2[CH:29]([CH3:31])[CH3:30])\[CH3:14])/[CH:3]=[CH:4]/[C:5](/[CH3:12])=[CH:6]/[C:7]([OH:9])=[O:8]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86759708ethyl (2E,4E,6E)-6-fluoro-7-(4-isopropyl-7-methoxy-2,2-dimethyl-2H-chromen-6-yl)-3-methyl-octa-2,4,6-trienoate2×

Product 1

HCID 22490881(2E,4E,6E)-6-Fluoro-7-(4-isopropyl-7-methoxy-2,2-dimethyl-2H-chromen-6-yl)-3-methyl-octa-2,4,6-trienoic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Following General Procedure G, a solution of ethyl (2E,4E,6E)-6-fluoro-7-(4-isopropyl-7-methoxy-2,2-dimethyl-2H-chromen-6-yl)-3-methyl-octa-2,4,6-trienoate (Compound 108, 116 mg, 2.71 mmol) in ethanol and THF was hydrolyzed with NaOH to yield a yellow oil after purification by column chromatography (silica gel, 100% hexane to 5% to 50% ethyl acetate in hexanesethyl). The resulting oil was recrystallized from acetonitrile to produce the title compound as a yellow solid.

Workup

  1. customto yield a yellow oil
  2. customafter purification by column chromatography (silica gel, 100% hexane to 5% to 50% ethyl acetate in hexanesethyl)
  3. customThe resulting oil was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-a2de77370f3c49598edc7cf64392abb3
Source dataset
uspto-grants-2005_05
Patent number
US06887896B1

Reaction notes

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