3,5-Dimethoxybenzaldehyde → 3,5-Dimethoxy-1-(1-propenyl)benzene

HRID 1060473Notes

Reaction equation

HRID 1060473 reaction equation
[Li][CH2:2][CH2:3]CC.[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:13]=[C:14]([O:16][CH3:17])[CH:15]=1)[CH:11]=O>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C.C1COCC1>[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:11]=[CH:2][CH3:3])[CH:13]=[C:14]([O:16][CH3:17])[CH:15]=1

Participants

5

Reactant 2

HCID 817473,5-DimethoxybenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 539005613,5-Dimethoxy-1-(1-propenyl)benzene

Reagents, catalysts & solvents 2

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)CatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

Ethyltriphenylphosphonium bromide (4.69 g) was dissolved in anhydrous THF (70 mL) and the mixture cooled to 0-5° C. n-BuLi (5.05 mL of 2.5 M in hexane) was added dropwise and the resulting mixture was stirred at room temperature for 3 h. The mixture was cooled to −78° C. and a solution of 3,5-dimethoxybenzaldehyde (2 g) in anhydrous THF (14 mL) was added. The mixture was allowed to warm up to room temperature then stirred overnight. The mixture was concentrated, and the residue was taken up with AcOEt, washed with water and brine, dried (MgSO4), filtered and evaporated. The residue was purified by column chromatography (silica gel; eluent: hexane and AcOEt 10:1) to give 3,5-dimethoxy-1-(1-propenyl)benzene as a mixture of cis and trans isomers (2.15 g).

Workup

  1. additionwas added dropwise
  2. temperatureThe mixture was cooled to −78° C.
  3. temperatureto warm up to room temperature
  4. stirringthen stirred overnight
  5. concentrationThe mixture was concentrated
  6. washwashed with water and brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified by column chromatography (silica gel; eluent: hexane and AcOEt 10:1)

Sources & evidence

ORD record
ord-9e1e4b08d9224fd1b64c525898ae5b21
Source dataset
uspto-grants-2003_02
Patent number
US06521666B1

Reaction notes

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