Magnesium perchlorate → Methyl 3-(3-benzyloxycarbonyl-4-methoxyphenyl)-2,2-dimethylpropanoate

HRID 1634524Notes

Reaction equation

HRID 1634524 reaction equation
C(O[CH2:5][C:6]1[CH:7]=[CH:8][C:9]([O:22][CH3:23])=[C:10]([CH:21]=1)[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])(=O)C.Cl([O-])(=O)(=O)=O.[Mg+2].Cl([O-])(=O)(=O)=O>C(Cl)Cl>[CH2:14]([O:13][C:11]([C:10]1[CH:21]=[C:6]([CH2:5][C:10]([CH3:21])([CH3:9])[C:11]([O:13][CH3:14])=[O:12])[CH:7]=[CH:8][C:9]=1[O:22][CH3:23])=[O:12])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 24840Magnesium perchlorateHCID 18678020Benzyl 5-acetoxymethyl-2-methoxybenzoate

Product 1

HCID 11057401Methyl 3-(3-benzyloxycarbonyl-4-methoxyphenyl)-2,2-dimethylpropanoateYield 36.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzyl 5-acetoxymethyl-2-methoxybenzoate (630 mg, 2.00 mmol), methyl trimethylsilyldimethylketeneacetal (730 mg, 4.02 mmol) and 25 ml of dehydrated methylene chloride were mixed and magnesium perchlorate (45 mg, 0.202 mmol) was added under an atmosphere of argon, which was stirred for 6 hours at room temperature. The reaction mixture was washed with water and with brine, then dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel chromatography (eluate n-hexane:ethyl acetate=8:1 v/v) to obtain 131 mg (18%) of the title compound as colorless crystals.

Workup

  1. washThe reaction mixture was washed with water and with brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography (eluate n-hexane:ethyl acetate=8:1 v/v)

Sources & evidence

ORD record
ord-b03ab1b33ea6439b9db17d781fd7a8de
Source dataset
uspto-grants-2003_01
Patent number
US06506797B1

Reaction notes

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