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

HRID 705155

Reaction equation

HRID 705155 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 to rt, and stirred for 1 h. The solvent was removed under reduced pressure to give crude product as an oil containing a 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 a significant amount of solid

Sources & evidence

ORD record
ord-8937b3131b5c4cc495e32f6b23a4c337
Source dataset
uspto-grants-2015_11
Patent number
US09173893B2

Linked notes

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