1-Naphthaldehyde → HCID 12192538, compound
Reaction equation
[C:1]1([CH:11]=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].[C:19]1(P(=O)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:24]=CC=C[CH:20]=1.[PH4+]>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C.CCCCCC.C1(C)C=CC=CC=1>[CH2:19]([CH:24]=[CH:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)[CH3:20]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
1-(ethyl)-2-(naphthyl)ethylene (IXd) was prepared from 1.00 g (2.7 mmol) of (ethyl)triphenylphosphonium bromide (Vd), 0.42 g (2.7 mmol) of naphthaldehyde and 0.79 g (5.5 mmol) of anhydrous K2CO3 by ball-milling for 26 hours. The formed powder was analyzed by the solid state 31P MAS NMR spectroscopy. The solid state 31P MAS NMR spectrum of the ball-milled powder contained two signals: a major signal corresponding to triphenylphosphine oxide at δ31P=25 ppm and a minor signal corresponding to the starting phosphonium salt at δ31P=30 ppm, the estimated ratio ˜8:1. The powder (2.0 g) was loaded on the top of a silica-gel filled chromatographic column, and the mixture of (E)- and (Z)-isomers was isolated by eluation with a hexane-toluene mixture (E:Z ratio ca. 1:1 by 1H NMR in CDCl3) in the 63% yield, (0.26 g). Triphenylphosphine oxide was further obtained from the same column in 80% yield (0.61 g) using a hexane-acetone mixture as an eluant. Assignment of the signals in the 13C and 1H NMR spectra of the reaction products was performed according to the literature (see, e.g., Kulasegarm, et al., J. Org. Chem. 62, 6547 (1997); Kulasegarm et al., Tetrahedron 54, 1361(1998)).
Workup
- additionfilled chromatographic column
Sources & evidence
- ORD record
- ord-553bbe0382de4df7b9cb1a9a271d6afc
- Source dataset
- uspto-grants-2004_05
- Patent number
- US06730812B2
Reaction notes
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