Triethylamine → HCID 86662556, compound

HRID 408961Notes

Reaction equation

HRID 408961 reaction equation
[P:1](Cl)([Cl:4])([Cl:3])=[O:2].[OH:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]([C@H:17]([CH3:22])[C:18]([O:20][CH3:21])=[O:19])[CH:11]=[CH:10]2.C(N(CC)CC)C>C(OCC)C>[Cl:3][P:1]([O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]([C@H:17]([CH3:22])[C:18]([O:20][CH3:21])=[O:19])[CH:11]=[CH:10]2)([Cl:4])=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 15086654HCID 15086654, compound

Product 1

HCID 86662556HCID 86662556, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Phosphorus oxychloride (0.202 mL, 1 equiv) and (S)-methyl 2-(6-hydroxynaphthalen-2-yl)propanoate (Aldrich, 500 mg, 1 equiv) were stirred in anhydrous diethyl ether (25 mL). Anhydrous triethylamine was added (0.302 mL, 1 equiv) at −78° C. and the solution was allowed to warm to room temperature after 25 min, the triethylamine hydrochloride salt was filtered off and the solvent was removed under reduced pressure to give a clear pale yellow thick syrup (750 mg, 95%).

Workup

  1. filtrationthe triethylamine hydrochloride salt was filtered off
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-1ea40148649d410bae7525569010e867
Source dataset
uspto-grants-2014_06
Patent number
US08759318B2

Reaction notes

Loading…