Trimethyl phosphite → HCID 10220583, compound

HRID 1440660Notes

Reaction equation

HRID 1440660 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1.[CH3:13][O:14][P:15]([O:18]C)[O:16][CH3:17]>C1(C)C=CC=CC=1>[CH3:13][O:14][P:15]([CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1)(=[O:18])[O:16][CH3:17]

Participants

4

Reactant 2

HCID 8472Trimethyl phosphite2×HCID 703202-Bromomethylnaphthalene

Product 1

HCID 10220583HCID 10220583, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2-bromomethylnaphthalene (4.42 g, 0.020 M) and trimethylphosphite (5 mL, 5.26 g, 0.042 M) in dry toluene (100 mL) is heated at reflux temperature for 120 hours The reaction is incomplete, so the volume of the solution is reduced to 25 mL, additional trimethylphosphite (5 mL) is added, and the solution heated to reflux for another 24 hours. Solvent is removed under reduced pressure and the solid white residue is chromatographed over silica gel (40-63 μm, 195 g, ethyl acetate). Elution of the column with ethyl acetate gave title compound (4.63 g) as a white solid which after crystallization from ether-hexane had mp 80°-81° C.

Workup

  1. temperatureat reflux temperature for 120 hours The reaction
  2. additionis added
  3. temperaturethe solution heated
  4. temperatureto reflux for another 24 hours
  5. customSolvent is removed under reduced pressure
  6. customthe solid white residue is chromatographed over silica gel (40-63 μm, 195 g, ethyl acetate)
  7. washElution of the column with ethyl acetate

Sources & evidence

ORD record
ord-f45038c79fdd4e44a0358dcb652dec2a
Source dataset
uspto-grants-1996_03
Patent number
US05500417

Reaction notes

Loading…