Triethyl phosphite → Diethyl ((thiophen-2-yl)methyl)phosphonate

HRID 1938934Notes

Reaction equation

HRID 1938934 reaction equation
[P:1]([O:8][CH2:9][CH3:10])([O:5][CH2:6][CH3:7])[O:2]CC.Cl[CH2:12][C:13]1[S:14][CH:15]=[CH:16][CH:17]=1>>[S:14]1[CH:15]=[CH:16][CH:17]=[C:13]1[CH2:12][P:1](=[O:2])([O:5][CH2:6][CH3:7])[O:8][CH2:9][CH3:10]

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 698302-(Chloromethyl)thiophene

Product 1

HCID 4185897Diethyl ((thiophen-2-yl)methyl)phosphonate

Conditions

Temperature
150 °C

Procedure

Following the general procedure for carrying out the Arbuzov reaction (reference cite: Chem. Rev. 81, 415, 1981) 0.1 mole (17.5 ml) of triethyl phosphite and 0.1 mole (13.2 g) of 2-chloromethylthiophene were combined and heated under N2 at 150° C. for 5 hours. The reaction mixture was cooled and partitioned between 100 ml methylene chloride and 50 ml. water. The organic phase was separated, washed with saturated NaHCO3 solution, dried over magnesium sulfate and concentrated under vacuum to yield 17.5 g. crude liquid product.

Workup

  1. temperatureThe reaction mixture was cooled
  2. custompartitioned between 100 ml methylene chloride and 50 ml
  3. customThe organic phase was separated
  4. washwashed with saturated NaHCO3 solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under vacuum
  7. customto yield 17.5 g

Sources & evidence

ORD record
ord-a413d14804cb4779ad17e34aa80f114f
Source dataset
uspto-grants-1997_12
Patent number
US05693809

Reaction notes

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