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

HRID 1198717Notes

Reaction equation

HRID 1198717 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-9823642ffc3c453189b6682e84aa9eea
Source dataset
uspto-grants-1994_01
Patent number
US05281685

Reaction notes

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