1,8-Diazabicyclo(5.4.0)undec-7-ene → 1-(2-Benzyloxyphenyl)-4-(3-chlorophenyl)butadiene

HRID 743399Notes

Reaction equation

HRID 743399 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=O)[CH:5]=[CH:6][CH:7]=1.[Cl-].[CH2:13]([O:20][C:21]1[CH:46]=[CH:45][CH:44]=[CH:43][C:22]=1[CH2:23][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.N12CCCN=C1CCCCC2>C(#N)C>[CH2:13]([O:20][C:21]1[CH:46]=[CH:45][CH:44]=[CH:43][C:22]=1[CH:23]=[CH:10][CH:9]=[CH:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27631113-(3-Chlorophenyl)prop-2-enalHCID 194239672-Benzyloxybenzyltriphenylphosphonium chloride

Product 1

HCID 545226781-(2-Benzyloxyphenyl)-4-(3-chlorophenyl)butadieneYield 94%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Following a procedure similar to that described in the first part of Preparation 3, the whole of this 3-(3-chlorophenyl)-2-propenal was reacted with 6.9 g of 2-benzyloxybenzyltriphenylphosphonium chloride (prepared as described in Preparation 1) and 2.89 g of 1,8-diazabicyclo[5,4,0]undec-7-ene in 100 ml of acetonitrile. The crude product, extracted as described in the first part of Preparation 3, was purified as described in the first part of Preparation 3, to give 4.13 g (yield 94%) of 1-(2-benzyloxyphenyl)-4-(3-chlorophenyl)butadiene as an oil.

Workup

  1. customthat described in the first part of Preparation 3
  2. extractionThe crude product, extracted
  3. customas described in the first part of Preparation 3
  4. customwas purified
  5. customas described in the first part of Preparation 3

Sources & evidence

ORD record
ord-9d499ca1328845e99ea443d258b77e96
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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