Trimethyl phosphite → HCID 15345723, compound

HRID 233433Notes

Reaction equation

HRID 233433 reaction equation
Cl[CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[CH3:13].[CH3:14][O:15][P:16]([O:19]C)[O:17][CH3:18]>>[CH3:13][C:4]1[CH:5]=[CH:6][C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[CH2:2][P:16](=[O:19])([O:17][CH3:18])[O:15][CH3:14]

Participants

3

Reactant 2

HCID 8472Trimethyl phosphiteHCID 811061-Chloromethyl-2-methylnaphthalene

Product 1

HCID 15345723HCID 15345723, compoundYield 59.1%

Procedure

A solution of 1-chloromethyl-2-methylnaphthalene (9.50 g, 0.050M) in trimethylphosphite (15 mL, 15.8 g, 0.13 M) is heated at reflux temperature for 48 hours. Excess trimethylphosphite is removed under reduced pressure, giving a yellow oil which is chromatographed over silica gel (40-63 μ, 400 g, 50 mL fractions) using ethyl acetate for elution of the column. Fractions 18-21 are pooled and after concentration gave a white solid (7.78 g). Recrystallization from ether-pentane gave title compound (6.94 g) as colorless crystals, mp 54°-57° C.

Workup

  1. temperatureat reflux temperature for 48 hours
  2. customExcess trimethylphosphite is removed under reduced pressure
  3. customgiving a yellow oil which
  4. customis chromatographed over silica gel (40-63 μ, 400 g, 50 mL fractions)
  5. washfor elution of the column
  6. concentrationafter concentration

Sources & evidence

ORD record
ord-feee0f4ff7094727a151f20b449ef602
Source dataset
uspto-grants-1997_01
Patent number
US05593980

Reaction notes

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