4-Methylphenyl-2-propenal → 3-(4-Methylphenyl)but-3-en-2-ol

HRID 1349359Notes

Reaction equation

HRID 1349359 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[CH2:11])[CH:9]=[O:10])=[CH:4][CH:3]=1.[CH3:12][Li]>C(OCC)C>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[CH2:11])[CH:9]([OH:10])[CH3:12])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 180009044-Methylphenyl-2-propenalHCID 178418348HCID 178418348, compound

Product 1

HCID 106308343-(4-Methylphenyl)but-3-en-2-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

2.34 g of aldehyde 38 is dissolved in 150 ml of diethyl ether and cooled to −78° C. under nitrogen. 20 ml of methyllithium solution (1.6 M in diethyl ether) is now added in drops. After 1.5 hours at this temperature, it is quenched with saturated ammonium chloride solution, extracted with ethyl acetate, washed with sodium chloride solution, dried on sodium sulfate, and the solvent is removed. The residue is purified by chromatography on silica gel with ethyl acetate/hexane, whereby in addition to 237 mg of starting material, 1.06 g of title compound 39 accumulates as a colorless oil.

Workup

  1. customAfter 1.5 hours at this temperature, it is quenched with saturated ammonium chloride solution
  2. extractionextracted with ethyl acetate
  3. washwashed with sodium chloride solution
  4. customdried on sodium sulfate
  5. customthe solvent is removed
  6. customThe residue is purified by chromatography on silica gel with ethyl acetate/hexane, whereby in addition to 237 mg of starting material, 1.06 g of title compound 39 accumulates as a colorless oil

Sources & evidence

ORD record
ord-e69562dd311c40f2811ccc912c511c91
Source dataset
uspto-grants-2007_05
Patent number
US07211680B2

Reaction notes

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