Acetone → HCID 86594540, compound

HRID 1816426Notes

Reaction equation

HRID 1816426 reaction equation
[CH2:1]([O:3][C:4](=[O:31])/[CH:5]=[C:6](\[CH3:30])/[CH:7]=[CH:8]/[CH:9]=[C:10](/[C:15]1[C:24]([OH:25])=[CH:23][C:22]2[C:21]([CH3:27])([CH3:26])[CH2:20][CH2:19][C:18]([CH3:29])([CH3:28])[C:17]=2[CH:16]=1)\[C:11]([F:14])([F:13])[F:12])[CH3:2].[C:32]([O-])([O-])=O.[K+].[K+].CI.CC(C)=O>CCOC(C)=O>[CH2:1]([O:3][C:4](=[O:31])/[CH:5]=[C:6](\[CH3:30])/[CH:7]=[CH:8]/[CH:9]=[C:10](/[C:15]1[C:24]([O:25][CH3:32])=[CH:23][C:22]2[C:21]([CH3:27])([CH3:26])[CH2:20][CH2:19][C:18]([CH3:29])([CH3:28])[C:17]=2[CH:16]=1)\[C:11]([F:13])([F:12])[F:14])[CH3:2]

Participants

6

Reactant 4

HCID 180AcetoneHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 20777215HCID 20777215, compound2×

Product 1

HCID 86594540HCID 86594540, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (2E,4E,6Z)-8,8,8-trifluoro-7-(3-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-3-methyl-octa-2,4,6-trienoic acid ethyl ester (Intermediate 5, 160 mg, 0.37 mmol), K2CO3 (253 mg, 1.83 mmol), MeI (0.12 mL, 1.83 mmol), and acetone (2 mL), was stirred at ambient temperature for overnight. The reaction mixture was diluted with EtOAc, washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (3% EtOAc-hexane) to produce the title compound and its 2-Z isomer as a 2:1 mixture (167 mg). Further purification by HPLC (2.5% EtOAc-hexane) afforded the title compound as a clear oil (87 mg, 53%).

Workup

  1. washwashed with brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash column chromatography on silica gel (3% EtOAc-hexane)

Sources & evidence

ORD record
ord-53bc7bc79ef849bfa2fbe02da4bc92c5
Source dataset
uspto-grants-2005_04
Patent number
US06884820B2

Reaction notes

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