Sodium Hydroxide → HCID 22491011, compound

HRID 2180530Notes

Reaction equation

HRID 2180530 reaction equation
[CH3:1][C:2]1([CH3:36])[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][C:6]([O:32][CH2:33][CH2:34][CH3:35])=[C:7](/[C:18](/[CH3:31])=[C:19](/[F:30])\[CH:20]=[CH:21]\[C:22](\[CH3:29])=[CH:23]\[C:24]([O:26]CC)=[O:25])[CH:8]=2)[O:3]1.[OH-].[Na+]>>[CH3:1][C:2]1([CH3:36])[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][C:6]([O:32][CH2:33][CH2:34][CH3:35])=[C:7](/[C:18](/[CH3:31])=[C:19](/[F:30])\[CH:20]=[CH:21]\[C:22](\[CH3:29])=[CH:23]\[C:24]([OH:26])=[O:25])[CH:8]=2)[O:3]1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 86759712HCID 86759712, compound2×

Product 1

HCID 22491011HCID 22491011, compound

Procedure

Following General Procedure G, ethyl (2E,4E,6E)-7-(2,2-dimethyl-4-phenyl-7-propoxy-2H-chromen-6-yl)-6-fluoro-3-methyl-octa-2,4,6-trienoate (Compound 115, 131 mg, 0.27 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-24af10af54024b91af542c2537492278
Source dataset
uspto-grants-2005_05
Patent number
US06887896B1

Reaction notes

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