1,8-Diazabicyclo(5.4.0)undec-7-ene → 4-(2-Naphthyl)-1-(2-benzyloxyphenyl)-1-butene

HRID 743396Notes

Reaction equation

HRID 743396 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][CH2:12][CH:13]=O.[Cl-].[CH2:16]([O:23][C:24]1[CH:49]=[CH:48][CH:47]=[CH:46][C:25]=1[CH2:26][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.N12CCCN=C1CCCCC2>C(#N)C>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][CH2:12][CH:13]=[CH:26][C:25]1[CH:46]=[CH:47][CH:48]=[CH:49][C:24]=1[O:23][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 101764123-(2-Naphthyl)propanalHCID 194239672-Benzyloxybenzyltriphenylphosphonium chloride

Product 1

HCID 536892464-(2-Naphthyl)-1-(2-benzyloxyphenyl)-1-buteneYield 82.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Following a procedure similar to that described in the first part of Preparation 3, 1.73 g of 3-(2-naphthyl)propanal prepared as described above, 4.65 g of 2-benzyloxybenzyltriphenylphosphonium chloride (prepared as described in Preparation 1) and 2.15 g of 1,8 -diazabicyclo[5,4,0]undec-7-ene were reacted in 200 ml of acetonitrile. The reaction mixture was worked up and purified as described in the first part of Preparation 3, to obtain 2.83 g (yield 82%) of 4-(2-naphthyl)-1-(2-benzyloxyphenyl)-1-butene as a colorless oil.

Workup

  1. customprepared
  2. custompurified
  3. customas described in the first part of Preparation 3

Sources & evidence

ORD record
ord-9c69bc0188464b8fa60decc38c779dc2
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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