Methyl iodide → [4-(Cyclopropylcarbonyl)pheny]methyl-propanedioic acid, dimethyl ester

HRID 48020Notes

Reaction equation

HRID 48020 reaction equation
[CH:1]1([C:4]([C:6]2[CH:11]=[CH:10][C:9]([CH2:12][C:13](OC)=O)=[CH:8][CH:7]=2)=[O:5])[CH2:3][CH2:2]1.CO[C:19](=[O:22])[O:20][CH3:21].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].IC>O1CCCC1.C(OCC)(=O)C.O>[CH:1]1([C:4]([C:6]2[CH:7]=[CH:8][C:9]([CH2:12][CH:13]([C:19]([O:20][CH3:21])=[O:22])[C:19]([O:20][CH3:21])=[O:22])=[CH:10][CH:11]=2)=[O:5])[CH2:2][CH2:3]1

Participants

8

Reactant 4

HCID 6328Methyl iodideHCID 12021Dimethyl CarbonateHCID 2724254Sodium bis(trimethylsilyl)amideHCID 12096482Methyl 2-(4-(cyclopropanecarbonyl)phenyl)acetate

Product 1

HCID 67524057[4-(Cyclopropylcarbonyl)pheny]methyl-propanedioic acid, dimethyl esterYield 21.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 4-(cyclopropylcarbonyl)benzeneacetic acid, methyl ester (1.5 g, 6.0 mmol) and dimethylcarbonate (930 mg, 10.3 mmol) in tetrahydrofuran (10 mL). Add 20 mL (20 mmol) of a 1.0 molar solution of sodium bis(trimethylsilyl)amide in tetrahydrofuran over 0.5 hours. Stir 3 days. Add iodomethane (5.3 g, 35 mmol). Stir 24 hours. Add water and ethyl acetate. Wash organic phase with brine, dry over anhydrous magnesium sulfate and concentrate. Purify by flash chromatography (50 g silica gel, ethyl acetate/heptane as eluent) to give the title compound (315 mg, 16%).

Workup

  1. stirringStir 24 hours
  2. dry with materialWash organic phase with brine, dry over anhydrous magnesium sulfate
  3. concentrationconcentrate
  4. customPurify by flash chromatography (50 g silica gel, ethyl acetate/heptane as eluent)

Sources & evidence

ORD record
ord-ef6ce2a02caa4769ae002aeff9a27a6a
Source dataset
uspto-grants-2004_03
Patent number
US06700012B2

Reaction notes

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