Water → 1-(2-Methoxyphenyl)pent-4-en-1-ol

HRID 379511Notes

Reaction equation

HRID 379511 reaction equation
[CH2:1]([Mg]Br)[CH2:2][CH:3]=[CH2:4].[CH:7](=[O:16])[C:8]1[C:9]([O:14][CH3:15])=[CH:10][CH:11]=[CH:12][CH:13]=1.O>C1COCC1>[OH:16][CH:7]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][CH3:15])[CH2:4][CH2:3][CH:2]=[CH2:1]

Participants

5

Reactant 3

HCID 962WaterHCID 86582-MethoxybenzaldehydeHCID 178418797HCID 178418797, compound

Product 1

HCID 158847211-(2-Methoxyphenyl)pent-4-en-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-butenylmagnesium bromide in THF (0.50 M, 200 mL) at 0° C. was added o-anisaldehyde (13.62 g, 100 mmol) in THF (20 mL) dropwise and the reaction mixture was heated under reflux for 1 hour. Water was added, the aqueous layer was extracted with ether (×4), and the combined organic layers were washed with brine, dried over MgSO4 and evaporated in vacuo to give the title compound. The crude product was used for Preparation 17 without purification. 1H NMR (CDCl3, 400 MHz) δ: 7.3 (2H), 6.9 (2H), 5.8 (2H), 4.8-5.1 (3H), 3.85 (3H, OMe), 2.5 (1H), 1.8-2.3 (4H).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 1 hour
  3. extractionthe aqueous layer was extracted with ether (×4)
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-e320eded109d4b04ad6f0a0ff8d0d0c9
Source dataset
uspto-grants-2001_10
Patent number
US06300316B1

Reaction notes

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