Potassium Carbonate → Ethyl-4-(2-methoxy-3-methylphenyl)-4-methyl-2-oxopentanoate

HRID 1444532Notes

Reaction equation

HRID 1444532 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][CH:6]=[CH:5][C:4]=1[C:10](O)([CH3:12])[CH3:11].[CH2:14]([O:16][C:17](=[O:25])[C:18]([O:20][Si](C)(C)C)=[CH2:19])[CH3:15].[Sn](Cl)(Cl)(Cl)Cl.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[CH2:14]([O:16][C:17](=[O:25])[C:18](=[O:19])[CH2:20][C:10]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([CH3:9])[C:3]=1[O:2][CH3:1])([CH3:12])[CH3:11])[CH3:15]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 24287Tin tetrachlorideHCID 111168062-Trimethylsilanyloxy-acrylic acid ethyl esterHCID 179891622-(2-Methoxy-3-methylphenyl)propan-2-ol

Product 1

HCID 17989129Ethyl-4-(2-methoxy-3-methylphenyl)-4-methyl-2-oxopentanoateYield 41.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

71.37 g (395.96 mmol) of 2-(2-methoxy-3-methylphenyl)-propan-2-ol and 149 g (791.92 mmol) of 2-trimethylsilanyloxyacrylic acid ethyl ester are introduced into 1.1 l of dichloromethane. At −78° C., 44.8 ml (379.91 mmol) of tin tetrachloride is added in drops, and the batch is then stirred for three hours at this low temperature. 1.4 l of semiconcentrated potassium carbonate solution is carefully added in drops, and the reaction mixture is thus brought to room temperature. The batch is filtered, and the filtrate is extracted three times with ethyl acetate. The combined organic extracts are washed with brine, dried on sodium sulfate, and the solvent is spun off. The residue is chromatographed several times on silica gel (mobile solvent ethyl acetate/hexane). 45.81 g (41.6%) of the desired compound is isolated.

Workup

  1. customis thus brought to room temperature
  2. filtrationThe batch is filtered
  3. extractionthe filtrate is extracted three times with ethyl acetate
  4. washThe combined organic extracts are washed with brine
  5. customdried on sodium sulfate
  6. customThe residue is chromatographed several times on silica gel (mobile solvent ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ea3f820ea9ec4d4bac5063e6db0c38bb
Source dataset
uspto-grants-2010_02
Patent number
US07662821B2

Reaction notes

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