Sodium Hydroxide → HCID 60003029, compound

HRID 2180478Notes

Reaction equation

[Cl:1][C:2]1[C:3]([O:30][CH3:31])=[C:4](/[C:17](/[CH3:29])=[CH:18]\[CH:19]=[CH:20]\[C:21](\[CH3:28])=[CH:22]\[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+]>>[Cl:1][C:2]1[C:3]([O:30][CH3:31])=[C:4](/[C:17](/[CH3:29])=[CH:18]\[CH:19]=[CH:20]\[C:21](\[CH3:28])=[CH:22]\[C:23]([OH:25])=[O:24])[CH:5]=[C:6]2[C:11]=1[O:10][C:9]([CH3:12])([CH3:13])[CH:8]=[C:7]2[CH:14]([CH3:16])[CH3:15]

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 87973121HCID 87973121, compound2×

Product 1

HCID 60003029HCID 60003029, compound

Procedure

Following General Procedure G, ethyl 7-(8-chloro-4-isopropyl-7-methoxy-2,2-dimethyl-2H-chromen-6-yl)-3-methyl-octa-2E,4E,6Z-trienoate (Compound 39, 53 mg, 0.12 mmol) was hydrolyzed with 1M NaOH. Purification by column chromatography (silica gel, 20% to 30% ethyl acetate in hexanes) followed by recrystallization from acetonitrile gave rise to the title compound as a light yellow solid.

Workup

customPurification by column chromatography (silica gel, 20% to 30% ethyl acetate in hexanes)
customfollowed by recrystallization from acetonitrile

Sources & evidence

ORD record: ord-acd5ab5f8be24a2bbc6d599670747125
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06887896B1

Reaction notes

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