1-(1-Naphthyl)-1-propyne → HCID 12453334, compound

HRID 1814383Notes

Reaction equation

HRID 1814383 reaction equation
[C:1]1([C:11]#[C:12][CH3:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1>C1COCC1.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[C:1]1([C:11]#[C:12][CH3:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:1]1(/[CH:11]=[CH:12]\[CH3:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 1

HCID 110410811-(1-Naphthyl)-1-propyne

Product 2

HCID 110410811-(1-Naphthyl)-1-propyneHCID 12453334HCID 12453334, compoundYield 2,000%

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 8028TetrahydrofuranSolvent

Procedure

1-(1-Naphthyl)-1-propyne was prepared by literature procedures (H. Kouzai, et al, Bull. Chem. Soc. Jpn., (1995), 398.). The 1-(1-naphthyl)-1-propyne (10.8 g, 0.065 mol) was dissolved in THF, Lindlar's catalyst was added, and the solution was placed under a hydrogen atmosphere. After the reduction was complete, the solvent was removed and replaced with ether. The ether solution was filtered though a plug of silica, and the solvent removed to give the (Z)-1-(1-naphthyl)-propene (11.01 g, 0.65 mol). NMR (CDCl3) 8.1-7.7 (3H, m), 7.6-7.3 (4H, m), 7.0-6.8 (1H, m), 6.2-5.9 (1H, m), 1.8-1.7 (3H, dd).

Workup

  1. customthe solvent was removed
  2. filtrationThe ether solution was filtered though a plug of silica
  3. customthe solvent removed

Sources & evidence

ORD record
ord-e02ae4e28aca42b4b0aed31eac105909
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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