Diiodomethane → HCID 66738885, compound

HRID 1888881Notes

Reaction equation

HRID 1888881 reaction equation
C(I)I.[CH2:4]([O:6][C:7](=[O:12])[CH2:8][C:9]([CH3:11])=[CH2:10])[CH3:5].[CH3:13]COC(C)=O>C(OCC)C>[CH2:4]([O:6][C:7](=[O:12])[CH2:8][C:9]1([CH3:13])[CH2:11][CH2:10]1)[CH3:5]

Participants

5

Reactant 3

HCID 6346DiiodomethaneHCID 8857Ethyl AcetateHCID 30140213-Butenoic acid, 3-methyl-, ethyl ester

Product 1

HCID 66738885HCID 66738885, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
60 °C

Procedure

Zn—Cu couple (10.726 g) suspended in diethyl ether (20 ml) was treated at RT under an argon atmosphere with CH2I2 (14.86 g) and 3-methyl-but-3-enoic acid ethyl ester (3.9 g) and heated in a closed reaction vial at 60° C. for 20 h. The mixture was then cooled to RT, AcOEt (50 ml) were added and reaction mixture was filtered. The filter cake was washed with AcOEt, the combined filtrates washed with water (125 ml), dried over MgSO4 and then evaporated (applying a 40 mbar vacuum). This gave the desired (1-methyl-cyclopropyl)-acetic acid ethyl ester (4.4 g) as a brown liquid that was essentially pure (according to NMR) and used directly in the next reaction step.

Workup

  1. temperatureThe mixture was then cooled to RT
  2. customreaction mixture
  3. filtrationwas filtered
  4. washThe filter cake was washed with AcOEt
  5. washthe combined filtrates washed with water (125 ml)
  6. dry with materialdried over MgSO4
  7. customevaporated (

Sources & evidence

ORD record
ord-b9e57d21bf1146769a2662ac0ab2e314
Source dataset
uspto-grants-2013_08
Patent number
US08501940B2

Reaction notes

Loading…