(Methoxymethyl)triphenylphosphonium bromide → 1-(2-Methoxyethenyl)-4-(1-methylbutyloxy)benzene

HRID 1769425Notes

Reaction equation

HRID 1769425 reaction equation
C([Li])CCC.[Br-].[CH3:7][O:8][CH2:9][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH3:29][CH:30]([O:34][C:35]1[CH:42]=[CH:41][C:38]([CH:39]=O)=[CH:37][CH:36]=1)[CH2:31][CH2:32][CH3:33]>CCCCCC.O1CCCC1>[CH3:7][O:8][CH:9]=[CH:39][C:38]1[CH:41]=[CH:42][C:35]([O:34][CH:30]([CH3:29])[CH2:31][CH2:32][CH3:33])=[CH:36][CH:37]=1

Participants

6

Reactant 3

HCID 2773654(Methoxymethyl)triphenylphosphonium bromideHCID 199306244-(1-Methylbutyloxy)benzaldehydeHCID 178418339Butyllithium

Product 1

HCID 537267651-(2-Methoxyethenyl)-4-(1-methylbutyloxy)benzene

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

A solution containing butyllithium dissolved in hexane was added to a solution containing 120 g of methoxymethyltriphenylphosphonium bromide dissolved in tetrahydrofuran (THF), in an atmosphere of argon, and the mixture was stirred for one hour at room temperature. A solution of the compound (30) dissolved in THF was added thereto and stirring was continued for two hours. The reaction solution was washed with water, was dried over magnesium sulfate, and was then concentrated. The residue was purified by column chromatography to obtain 1-(2-methoxyethenyl)-4-(1-methylbutyloxy)benzene (31).

Workup

  1. additionwas added to a solution
  2. additionwas added
  3. stirringstirring
  4. waitwas continued for two hours
  5. washThe reaction solution was washed with water
  6. dry with materialwas dried over magnesium sulfate
  7. concentrationwas then concentrated
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-8d833bd498db432498c9cbaaf963bb50
Source dataset
uspto-grants-1995_01
Patent number
US05380915

Reaction notes

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