1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 54052906, compound

HRID 743391Notes

Reaction equation

HRID 743391 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][CH2:16][CH:17]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[CH3:20][O:21][CH2:22][O:23][C:24]1[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=1[CH2:26][PH3+].N12CCCN=C1CCCCC2>C(#N)C>[CH3:20][O:21][CH2:22][O:23][C:24]1[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=1[CH:26]=[CH:17][CH2:16][CH2:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 194238382-(Phenylmethoxy)benzenepropanalHCID 19423914HCID 19423914, compound

Product 1

HCID 54052906HCID 54052906, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Following a procedure similar to that described in the first part of Preparation 3, 2.51 g of 3-(2-benzyloxyphenyl)propanal, 5.6 g of 2-methoxymethoxybenzylphosphonium chloride (prepared as described in Preparation 2) and 1.91 g of 1,8-diazabicyclo[5,4,0]-undec-7-ene were reacted in 50 ml of acetonitrile. The crude product, extracted as described in the first part of Preparation 3, was purified by column chromatography through silica gel, using a 10:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 2.52 g (yield 64%) of 1-(2-methoxymethoxyphenyl)-4-(2-benzyloxyphenyl)-1-butene as a colorless oil.

Workup

  1. extractionThe crude product, extracted
  2. customas described in the first part of Preparation 3
  3. customwas purified by column chromatography through silica gel
  4. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-800dc1595ee74d4a8fb11bdfb32643c7
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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