Sodium Hydroxide → (2E,4E,6E)-7-(7-Ethoxy-2,2-dimethyl-4-phenyl-2H-chromen-6-yl)-6-fluoro-3-methyl-octa-2,4,6-trienoic acid

HRID 2180529Notes

Reaction equation

HRID 2180529 reaction equation
[CH2:1]([O:3][C:4]1[CH:13]=[C:12]2[C:7]([C:8]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:9][C:10]([CH3:15])([CH3:14])[O:11]2)=[CH:6][C:5]=1/[C:22](/[CH3:35])=[C:23](/[F:34])\[CH:24]=[CH:25]\[C:26](\[CH3:33])=[CH:27]\[C:28]([O:30]CC)=[O:29])[CH3:2].[OH-].[Na+]>>[CH2:1]([O:3][C:4]1[CH:13]=[C:12]2[C:7]([C:8]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:9][C:10]([CH3:15])([CH3:14])[O:11]2)=[CH:6][C:5]=1/[C:22](/[CH3:35])=[C:23](/[F:34])\[CH:24]=[CH:25]\[C:26](\[CH3:33])=[CH:27]\[C:28]([OH:30])=[O:29])[CH3:2]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 86759711ethyl (2E,4E,6E)-7-(7-ethoxy-2,2-dimethyl-4-phenyl-2H-chromen-6-yl)-6-fluoro-3-methyl-octa-2,4,6-trienoate2×

Product 1

HCID 22490834(2E,4E,6E)-7-(7-Ethoxy-2,2-dimethyl-4-phenyl-2H-chromen-6-yl)-6-fluoro-3-methyl-octa-2,4,6-trienoic acid

Procedure

Following General Procedure G, a solution of ethyl (2E,4E,6E)-7-(7-ethoxy-2,2-dimethyl-4-phenyl-2H-chromen-6-yl)-6-fluoro-3-methyl-octa-2,4,6-trienoate (Compound 114, 147 mg, 0.31 mmol) 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 hexanes). 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 hexanes)
  3. customThe resulting oil was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-8d1fcc28bc354935bfb37d4c1f338ed8
Source dataset
uspto-grants-2005_05
Patent number
US06887896B1

Reaction notes

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