Dimethyl Sulfide → HCID 19707469, compound

HRID 726917Notes

Reaction equation

HRID 726917 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=1)[C:7]([O:9][CH3:10])=[O:8].Br[C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=[O:19].S(C)C>N1C=CC=CC=1.O.C(OCC)(=O)C>[C:7]([C:6]1[CH:5]=[C:4]([O:3][C:15]2[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=2)[CH:18]=[O:19])[CH:13]=[CH:12][CH:11]=1)([O:9][CH3:10])=[O:8]

Participants

8

Reactant 4

HCID 1068Dimethyl SulfideHCID 24758Sodium hydrideHCID 765833-BromobenzaldehydeHCID 88068Methyl 3-Hydroxybenzoate

Product 1

HCID 19707469HCID 19707469, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of NaH (washed with hexane, 564 mg) in 20 mL of pyridine at 0° C. was added methyl 3-hydroxybenzoate (1.95 g), and the solution was allowed to warm to room temperature. After 5 minutes, 3-bromobenzaldehyde (1.64 mL) was added, then CuBr.SMe2 (3.15 g). The solution was heated to reflux under a stream of nitrogen. After 24 h, the reaction was cooled to room temperature and poured into ethyl acetate and water. The organic layer was washed twice with 10% aq. HCl solution, then with sat. aq. NaHCO3 solution, then with brine. The solution was dried (Na2SO4), filtered, and concentrated in vacuo to provide the crude product. Purification by silica gel chromatography (CH2 Cl2) gave the titled compound as a yellow oil.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux under a stream of nitrogen
  3. waitAfter 24 h
  4. temperaturethe reaction was cooled to room temperature
  5. washThe organic layer was washed twice with 10% aq. HCl solution
  6. dry with materialThe solution was dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto provide the crude product
  10. customPurification by silica gel chromatography (CH2 Cl2)

Sources & evidence

ORD record
ord-418521a60ed74301bf93afbfef49f43d
Source dataset
uspto-grants-1998_01
Patent number
US05710171

Reaction notes

Loading…