Methyl iodide → Methyl tropate

HRID 1760040Notes

Reaction equation

HRID 1760040 reaction equation
[C:1]([OH:12])(=[O:11])[CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:3][OH:4].[CH2:13](Cl)Cl.C1CCN2C(=NCCC2)CC1.CI>C1(C)C=CC=CC=1.O>[CH3:13][O:11][C:1](=[O:12])[CH:2]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)[CH2:3][OH:4]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 6344DichloromethaneHCID 10726Tropic acidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 239086Methyl tropateYield 18%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a solution of tropic acid (5.0 g, 30 mmol) in toluene:CH2Cl2 (150 mL; 2:1) was added DBU (4.6 g; 30 mmol), followed by MeI (4.3 g; 30 mmol). The mixture was stirred overnight, water was added and the phases were allowed to separate. The water phase was extracted with ether, and the combined organic phase was washed with NaHCO3/aq, HCl/aq and water, dried (Na2SO4) and concentrated to yield 0.95 g (18%) of the sub-title compound.

Workup

  1. customto separate
  2. extractionThe water phase was extracted with ether
  3. washthe combined organic phase was washed with NaHCO3/aq, HCl/aq and water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1faf057a4e78411eb5088aa8cfed6e6e
Source dataset
uspto-grants-2005_01
Patent number
US06838478B2

Reaction notes

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