Isopropanol → HCID 22393696, compound

HRID 1071619Notes

Reaction equation

HRID 1071619 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4](S(O)(=O)=O)=[CH:3][CH:2]=1.[CH:12]([OH:15])(C)[CH3:13]>O>[CH3:6][CH:1]([CH2:2][CH3:3])[CH:11]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:13][CH:12]=[O:15]

Participants

4

Reactant 2

HCID 3776IsopropanolHCID 6101p-Toluenesulfonic acid

Product 1

HCID 22393696HCID 22393696, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under a nitrogen atmosphere, a n-butyllithium/tetrahydrofuran solution (1.53 M, 1.2 mL) was added to a tetrahydrofuran solution of (methoxymethyl) triphenylphosphonium chloride (627 mg) at −78° C., and then the temperature of the mixture was raised to 0° C. After 20 minutes, the outer temperature was lowered to −78° C., and then 4-methyl-3-phenyl-pentanal (200 mg) was added thereto together with tetrahydrofuran (4 mL). After 45 minutes, the temperature of the mixture was returned to room temperature, and the mixture was further stirred for 20 minutes. The organic layer was separated by adding diethyl ether and an aqueous saturated ammonium chloride thereto. The resulting organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. After filtering off the drying agent, the mixture was evaporated, to give the title compound as a colorless oil (200 mg). The resulting compound was dissolved in isopropanol (2 mL)/water (2 mL), p-toluenesulfonic acid (6 mg) was added thereto, and then the reaction was carried outfor 8.5 hours under refluxing. The organic layer was separated by adding diethyl ether and an aqueous saturated ammonium chloride thereto. The resulting organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. After filteringoff thedryingagent, themixturewasevaporated. The residue was purified by NH silica gel column chromatography (hexane:ethyl acetate system), to give the title compound as a colorless oil (103 mg, 59%, 3 steps).

Workup

  1. additionwas added
  2. temperatureunder refluxing
  3. customThe organic layer was separated
  4. additionby adding diethyl ether
  5. washThe resulting organic layer was washed with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe residue was purified by NH silica gel column chromatography (hexane:ethyl acetate system)

Sources & evidence

ORD record
ord-6cee997c1ccf4a3eaba9642de4d2c29c
Source dataset
uspto-grants-2005_06
Patent number
US06906072B1

Reaction notes

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