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Toluene → 2-(4-Cyclopropyl-2,6-dimethyl-phenyl)-4-(tetrahydropyran-4-ylmethyl)-cyclopentane-1,3-dione

HRID 509173
Notes
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Reaction equation

HRID 509173 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH:9]2[C:13](=[O:14])[CH:12]([CH2:15][CH:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[CH2:11][C:10]2=[O:22])=[C:4]([CH3:23])[CH:3]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH:32]1(B(O)O)[CH2:34][CH2:33]1.C1(C)C=CC=CC=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C(COC)OC>[CH:32]1([C:2]2[CH:7]=[C:6]([CH3:8])[C:5]([CH:9]3[C:13](=[O:14])[CH:12]([CH2:15][CH:16]4[CH2:21][CH2:20][O:19][CH2:18][CH2:17]4)[CH2:11][C:10]3=[O:22])=[C:4]([CH3:23])[CH:3]=2)[CH2:34][CH2:33]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 1140TolueneHCID 62657Potassium Phosphate, TribasicHCID 2760897Cyclopropylboronic acidHCID 584814642-(4-Bromo-2,6-dimethylphenyl)-4-(tetrahydropyran-4-ylmethyl)cyclopentane-1,3-dione

Product 1

HCID 584815142-(4-Cyclopropyl-2,6-dimethyl-phenyl)-4-(tetrahydropyran-4-ylmethyl)-cyclopentane-1,3-dioneYield 13.6%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 2-(4-bromo-2,6-dimethylphenyl)-4-(tetrahydropyran-4-ylmethyl)cyclopentane-1,3-dione (0.1 g, 0.26 mmol), potassium phosphate (0.11 g, 0.53 mmol), cyclopropyl boronic acid (0.09 g, 1.05 mmol) and tetrakis(triphenylphosphine)palladium (0) (0.06 g, 0.053 mmol), toluene (2 ml), dimethoxyethane (0.5 ml) and water (0.5 ml) is heated under microwave conditions at 130° C. for 22 minutes. The organic solvent is evaporated under vacuo, diluted with water and extracted with ethylacetate (3×25 ml). The combined organic extracts are combined, washed with water and brine, dried over anhydrous sodium sulphate, filtered and the filtrate is concentrated in vacuo. The residue is purified by column chromatography on silica gel followed by preparative HPLC to give 2-(4-cyclopropyl-2,6-dimethyl-phenyl)-4-(tetrahydropyran-4-ylmethyl)-cyclopentane-1,3-dione (0.012 g).

Workup

  1. customThe organic solvent is evaporated under vacuo
  2. additiondiluted with water
  3. extractionextracted with ethylacetate (3×25 ml)
  4. washwashed with water and brine
  5. dry with materialdried over anhydrous sodium sulphate
  6. filtrationfiltered
  7. concentrationthe filtrate is concentrated in vacuo
  8. customThe residue is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-34a7c39a85b44dda8cd278f930f21ca4
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09096560B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes