Triethylamine → Methyl 3-(2-(dichlorophosphoryloxy)phenyl)propanoate

HRID 2408269Notes

Reaction equation

HRID 2408269 reaction equation
C(N(CC)CC)C.[OH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18].[P:21](Cl)([Cl:24])([Cl:23])=[O:22]>CCOCC>[Cl:23][P:21]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])([Cl:24])=[O:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 2794569Methyl 3-(2-hydroxyphenyl)propionate

Product 1

HCID 86661958Methyl 3-(2-(dichlorophosphoryloxy)phenyl)propanoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Dry triethylamine (0.38 mL, 2.8 mmol) and methyl 3-(2-hydroxyphenyl)propanoate, 80 (0.5 g, 2.77 mmol) in dry ether (9.2 mL) were added dropwise to a solution of dry ether (5 mL) containing phosphorus oxychloride (0.25 mL, 2.8 mmol) at −78° C. under nitrogen. Following the addition, the reaction mixture was slowly allowed to warm at room temperature, and stirred for 1 h. The solvent was removed under reduced pressure to give crude product as an oil containing significant amount of solid.

Workup

  1. additionthe addition
  2. customThe solvent was removed under reduced pressure
  3. customto give crude product as an oil
  4. additioncontaining significant amount of solid

Sources & evidence

ORD record
ord-84e02affd36549a493186bf733d1e096
Source dataset
uspto-grants-2014_08
Patent number
US08815829B2

Reaction notes

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