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

HRID 1869451Notes

Reaction equation

HRID 1869451 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 while being cooled slightly, and it is stirred vigorously for 20 minutes. After 2× extraction 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
  4. temperaturewhile being cooled slightly
  5. stirringit is stirred vigorously for 20 minutes
  6. extractionAfter 2× extraction with diethyl ether (800 ml each)
  7. washthe combined organic phases are washed with water and brine
  8. customis chromatographed on silica gel (mobile solvent ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ccb7896600ba45ba8dee71b55ccf614d
Source dataset
uspto-grants-2009_12
Patent number
US07638515B2

Reaction notes

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