Diisopropylamine → 1-Cyclopentyl-5-(4-hydroxy-2,5-dimethyl-phenyl)-pent-4-yn-1-one

HRID 858860

Reaction equation

HRID 858860 reaction equation
[CH:1]1([C:6](=[O:11])[CH2:7][CH2:8][C:9]#[CH:10])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N[CH:16]([CH3:18])[CH3:17])(C)C>CN(C=O)C.CCOC(C)=O.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:1]1([C:6](=[O:11])[CH2:7][CH2:8][C:9]#[C:10][C:3]2[CH:2]=[C:1]([CH3:5])[C:6]([OH:11])=[CH:18][C:16]=2[CH3:17])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 2

HCID 7912DiisopropylamineHCID 224997991-Cyclopentyl-pent-4-yn-1-one

Product 1

HCID 587625021-Cyclopentyl-5-(4-hydroxy-2,5-dimethyl-phenyl)-pent-4-yn-1-oneYield 19%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-cyclopentyl-pent-4-yn-1-one (0.33 g, 2.2 mmol) from example F(7), Step 2,4-iodo-2,5-dimethyl-phenol (0.54 g, 2.2 mmol), copper (I) iodide (33 mg, 0.18 mmol), trans-dichlorobis(triphenylphosphine)palladium (II) (63 mg, 0.09 mmol), and diisopropylamine (2.2 mL) in DMF (2.2 mL) was heated to 100° C. for 30 minutes. The reaction was cooled to room temperature and diluted with 10 mL of EtOAc. The resulting slurry was filtered, and the mother liquor was concentrated to a black oil. The oil was then purified by flash chromatography to give the desired product (112 mg, 19% yield).

Workup

  1. customwas heated to 100° C. for 30 minutes
  2. filtrationThe resulting slurry was filtered
  3. concentrationthe mother liquor was concentrated to a black oil
  4. customThe oil was then purified by flash chromatography

Sources & evidence

ORD record
ord-254ee27bfed648038d4dfd2fcebf474e
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Linked notes

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