Acetone → HCID 86594541, compound

HRID 1816427Notes

Reaction equation

HRID 1816427 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([O-])([O-])=O.[K+].[K+].[CH2:38](I)[CH3:39].CC(C)=O>CCOC(C)=O.CCCCCC>[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][CH2:38][CH3:39])=[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 6340IodoethaneHCID 11430Potassium CarbonateHCID 20777215HCID 20777215, compound2×

Product 1

HCID 86594541HCID 86594541, compound

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Following General Procedure A and using (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), EtI (0.15 mL, 1.83 mmol), and acetone (2 mL) followed by HPLC (2.5% EtOAc-hexane), the title compound was obtained as a clear syrup (81 mg, 48%).

Sources & evidence

ORD record
ord-9d11682fdeff4d9bb7313ef4f8f52cf5
Source dataset
uspto-grants-2005_04
Patent number
US06884820B2

Reaction notes

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