Dimethylformamide → 2-(6-Methoxynaphthalen-2-yl)propanoyl chloride

HRID 335663Notes

Reaction equation

HRID 335663 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]([C@H:17]([CH3:21])[C:18](O)=[O:19])[CH:11]=[CH:10]2.CN(C=O)C>C(Cl)(Cl)Cl>[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]([C@H:17]([CH3:21])[C:18]([Cl:3])=[O:19])[CH:11]=[CH:10]2

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 156391Naproxen

Product 1

HCID 54916922-(6-Methoxynaphthalen-2-yl)propanoyl chlorideYield 88.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Compound 2 was prepared from the corresponding carboxylic acid. Thionyl chloride (1.24 g, 10.42 mmoles) was added to a solution of (S)-(+)-2-(6-methoxy-naphthalen-2-yl)-propionic acid (Naproxen, 2 g, 8.69 mmoles) in 8.2 mL chloroform in a round bottom flask equipped with magnetic stirring. A drop of DMF was added and the mixture was refluxed for 3 hours. Chloroform and excess thionyl chloride were distilled from the reaction mixture while methylene chloride was added. Evaporation of residual solvent yielded (S)-2-(6-methoxy-naphthalen-2-yl)-propionyl chloride (1.918 g, 88.8% yield). Rf=0.2 (1:1 hexanes:ethyl ether). 1H NMR (400 MHz, CDCl3) δ 9.98 (br, 1H), 7.78 (t, 2H), 7.36 (d, 1H), 7.18 (d, 1H), 7.14 (m, 2H), 4.25 (q, 1H), 3.93 (s, 3H), 1.68 (d, 3H).

Workup

  1. customequipped with magnetic stirring
  2. temperaturethe mixture was refluxed for 3 hours
  3. distillationChloroform and excess thionyl chloride were distilled from the reaction mixture while methylene chloride
  4. additionwas added
  5. customEvaporation of residual solvent

Sources & evidence

ORD record
ord-20fdeaec27664a1d8a3f50b8a635582c
Source dataset
uspto-grants-2014_11
Patent number
US08884060B2

Reaction notes

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