Sodium Hydroxide → HCID 90961793, compound

HRID 2180552Notes

Reaction equation

HRID 2180552 reaction equation
[Cl:1][C:2]1[C:3]([O:32][CH:33]([CH3:35])[CH3:34])=[C:4](/[C:17](/[CH2:30][CH3:31])=[CH:18]/[CH:19]=[CH:20]/[C:21](/[CH3:29])=[C:22](/[F:28])\[C:23]([O:25]CC)=[O:24])[CH:5]=[C:6]2[C:11]=1[O:10][C:9]([CH3:13])([CH3:12])[CH:8]=[C:7]2[CH:14]([CH3:16])[CH3:15].[OH-].[Na+]>C(O)C.C1COCC1>[Cl:1][C:2]1[C:3]([O:32][CH:33]([CH3:34])[CH3:35])=[C:4]([C:17]([CH2:30][CH3:31])=[CH:18][CH:19]=[CH:20][C:21]([CH3:29])=[C:22]([F:28])[C:23]([OH:25])=[O:24])[CH:5]=[C:6]2[C:11]=1[O:10][C:9]([CH3:13])([CH3:12])[CH:8]=[C:7]2[CH:14]([CH3:15])[CH3:16]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 87972284HCID 87972284, compound2×

Product 1

HCID 90961793HCID 90961793, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Following General Procedure G, a solution of ethyl 7-(8-chloro-7-isopropoxy-4-isopropyl-2,2-dimethyl-2H-chromen-6-yl)-2-fluoro-3-methyl-nona-2E,4E,6E-trienoate (Compound 169, 1.02 g, 2.01 mmol) in ethanol and THF was hydrolyzed with 1M NaOH. Purification by flash chromatography (silica gel, 30% to 50% ethyl acetate in hexanes) and recrystallization from acetonitrile gave rise to the title compound as a pale yellow solid.

Workup

  1. customPurification
  2. customby flash chromatography (silica gel, 30% to 50% ethyl acetate in hexanes) and recrystallization from acetonitrile

Sources & evidence

ORD record
ord-7aeb9f80ea114385b7fab6a3bcf80979
Source dataset
uspto-grants-2005_05
Patent number
US06887896B1

Reaction notes

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