Ethanol → HCID 22493858, compound

HRID 1816430Notes

Reaction equation

HRID 1816430 reaction equation
C([O:3][C:4](=[O:34])/[CH:5]=[C:6](\[CH3:33])/[CH:7]=[CH:8]/[CH:9]=[C:10](/[C:15]1[C:24]([O:25][CH2:26][CH2:27][CH3:28])=[CH:23][C:22]2[C:21]([CH3:30])([CH3:29])[CH2:20][CH2:19][C:18]([CH3:32])([CH3:31])[C:17]=2[CH:16]=1)\[C:11]([F:14])([F:13])[F:12])C.[OH-].[Na+].CCO>CCOC(C)=O.CCCCCC>[F:12][C:11]([F:13])([F:14])/[C:10](/[C:15]1[C:24]([O:25][CH2:26][CH2:27][CH3:28])=[CH:23][C:22]2[C:21]([CH3:30])([CH3:29])[CH2:20][CH2:19][C:18]([CH3:32])([CH3:31])[C:17]=2[CH:16]=1)=[CH:9]\[CH:8]=[CH:7]\[C:6](\[CH3:33])=[CH:5]\[C:4]([OH:34])=[O:3]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 86594544HCID 86594544, compound2×

Product 1

HCID 22493858HCID 22493858, compound

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Following General Procedure B and using (2E,4E,6Z)-8,8,8-trifluoro-3-methyl-7-(5,5,8,8-tetramethyl-3-propoxy-5,6,7,8-tetrahydro-naphthalen-2-yl)-octa-2,4,6-trienoic acid ethyl ester (Compound 3, 83 mg, 0.17 mmol), 1M NaOH (0.35 mL), and EtOH (3 mL) at 60° C. for 1.5 h followed by flash column chromatography on silica gel (30% EtOAc-hexane) and HPLC (15% EtOAc-hexane), the title compound was obtained as a white solid (60 mg, 77%).

Workup

  1. customat 60° C.
  2. customfor 1.5 h

Sources & evidence

ORD record
ord-e5c8a6ecb5b9468486ef445f5dad0e32
Source dataset
uspto-grants-2005_04
Patent number
US06884820B2

Reaction notes

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