1-Octyne → HCID 67258438, compound

HRID 2423376Notes

Reaction equation

HRID 2423376 reaction equation
[CH:1]#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].I[C:10]1[CH:22]=[CH:21][C:13]([CH2:14][CH:15]2[CH2:19][CH2:18][CH2:17][C:16]2=[O:20])=[CH:12][CH:11]=1>C1COCC1>[C:1]([C:10]1[CH:22]=[CH:21][C:13]([CH2:14][CH:15]2[CH2:19][CH2:18][CH2:17][C:16]2=[O:20])=[CH:12][CH:11]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

4

Reactant 2

HCID 123701-OctyneHCID 6426224HCID 6426224, compound

Product 1

HCID 67258438HCID 67258438, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.1 g (10 mmol) of 1-Octyne was added to a flame dried 25 mL flask charged with a 10 mL THF solution of 1.49 g (5 mmol) of 2-(4′-iodobenzyl)cyclopentanone (3). After degassing for 30 minutes, 2 mL triethylamine, 5 mg of CuI and 10 mg of Pd(PPh3)4 were added under N2 protection. The reaction was stirred at room temperature for 6 hrs, then the solvent removed in vacuo and residue chromotographed with chloroform eluent to give 1.25 g (93%) as a yellow oil.

Workup

  1. customdried 25 mL flask
  2. customAfter degassing for 30 minutes
  3. addition2 mL triethylamine, 5 mg of CuI and 10 mg of Pd(PPh3)4 were added under N2 protection
  4. customthe solvent removed in vacuo and residue
  5. customto give 1.25 g (93%) as a yellow oil

Sources & evidence

ORD record
ord-9c584ee0e7d14b4f96bbdaba340bb94b
Source dataset
uspto-grants-2011_06
Patent number
US07960588B2

Reaction notes

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