Dimethyl Sulfoxide → Ethyl-4-(3-methoxyphenyl)-4-methyl-2-oxopentanoate

HRID 1443270Notes

Reaction equation

HRID 1443270 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]([CH3:19])([CH3:18])[CH2:10][CH:11]([OH:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:6]=[CH:7][CH:8]=1.CS(C)=O.C(N(CC)CC)C>ClCCl>[CH2:15]([O:14][C:12](=[O:13])[C:11](=[O:17])[CH2:10][C:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)([CH3:19])[CH3:18])[CH3:16]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 17989103Ethyl-4-(3-methoxyphenyl)-2-hydroxy-4-methylpentanoate

Product 1

HCID 17989270Ethyl-4-(3-methoxyphenyl)-4-methyl-2-oxopentanoateYield 75.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2019 g (78.47 mmol) of ethyl 4-(3-methoxyphenyl)-2-hydroxy-4-methyl-pentanoate is dissolved in 820 ml of dichloromethane and mixed with 273 ml of dimethyl sulfoxide. After 39.7 g (392.36 mmol) of triethylamine is added, the batch is mixed in portions with 31.2 g (196.18 mmol) of SO3/pyridine complex and then stirred for 16 hours at room temperature. About 400 ml of dichloromethane is drawn off in a rotary evaporator. Then, the reaction mixture is mixed with 312 ml of saturated ammonium chloride solution with slight cooling, and it is stirred vigorously for 20 minutes. After being extracted two times with diethyl ether (800 ml each), the combined organic phases are washed with water and brine. The residue that remains after the solvent is spun off is chromatographed on silica gel (mobile solvent: ethyl acetate/hexane). 15.59 g (75.3%) of the desired compound is isolated.

Workup

  1. additionthe batch is mixed in portions with 31.2 g (196.18 mmol) of SO3/pyridine complex
  2. customAbout 400 ml of dichloromethane is drawn off in a rotary evaporator
  3. additionThen, the reaction mixture is mixed with 312 ml of saturated ammonium chloride solution with slight cooling, and it
  4. stirringis stirred vigorously for 20 minutes
  5. extractionAfter being extracted two times with diethyl ether (800 ml each)
  6. washthe combined organic phases are washed with water and brine
  7. customis chromatographed on silica gel (mobile solvent: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c8261ccd488b4e608e04c4b6b52a6454
Source dataset
uspto-grants-2010_02
Patent number
US07659297B2

Reaction notes

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