Triethylamine → HCID 58875073, compound

HRID 130371Notes

Reaction equation

HRID 130371 reaction equation
Br[C:2]([CH3:8])([C:4](=[O:7])[CH2:5][CH3:6])[CH3:3].[SH:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].C(N(CC)CC)C>C(Cl)Cl>[CH2:14]([O:13][C:11](=[O:12])[CH2:10][S:9][C:2]([CH3:8])([CH3:3])[C:4](=[O:7])[CH2:5][CH3:6])[CH3:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12185Ethyl ThioglycolateHCID 12636562HCID 12636562, compound

Product 1

HCID 58875073HCID 58875073, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-bromo-2-methyl-pentan-3-one (A1) (13.5 g, 75 mmol) in CH2Cl2 (400 ml) were added ethyl 2-mercaptoacetate (9 g, 8.2 ml, 75 mmol) and 10.42 ml triethylamine at 0° C. and stirred for 3 h. The solution was allowed to come to room temperature (12 h). The resulting suspension was filtered, the filtrate washed with water (100 ml) and brine (100 ml) and dried over Na2SO4. Removal of the solvent in vacuo gave a slightly yellow oil, which was purified by flash chromatography (ethyl acetate-petroleum ether 1:25).

Workup

  1. customto come to room temperature
  2. custom(12 h)
  3. filtrationThe resulting suspension was filtered
  4. washthe filtrate washed with water (100 ml) and brine (100 ml)
  5. dry with materialdried over Na2SO4
  6. customRemoval of the solvent in vacuo
  7. customgave a slightly yellow oil, which
  8. customwas purified by flash chromatography (ethyl acetate-petroleum ether 1:25)

Sources & evidence

ORD record
ord-0887e704ed474c1b9aa5d068c00fefe0
Source dataset
uspto-grants-2008_06
Patent number
US07381743B2

Reaction notes

Loading…