2-Naphthaleneacetic acid → 2-(2-Naphthyl)acetyl chloride

HRID 1005423

Reaktionsgleichung

Reaktionsgleichung von HRID 1005423
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][C:12]([OH:14])=O.C(Cl)(=O)C([Cl:18])=O>C(Cl)Cl.CN(C=O)C>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][C:12]([Cl:18])=[O:14]

Komponenten

5

Edukt 2

HCID 113932-Naphthaleneacetic acidHCID 65578Oxalyl chloride

Produkt 1

HCID 5881152-(2-Naphthyl)acetyl chloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-naphthylacetic acid (0.960 g, 5.15 mmol) in methylene chloride (10 mL) was added oxalyl chloride (0.58 mL, 6.7 mmol) and DMF (1 drop). After 1.5 hours, the solvent was evaporated to give 2-naphthylacetyl chloride. A solution of the 2-naphthylacetyl chloride in THF (3 mL), cooled to -78° C., was slowly cannulated into a stirred solution of the lithium salt of 4 -(S)-(+)-4-isopropyl-2-oxazolidinone (prepared by treating, at -78° C., a solution of 4 -(S)-(+)-4 -isopropyl-2-oxazolidinone (0.60 g, 5.2 mmol) in THF (4 mL) with a solution of butyllithium (1.6 M in hexane) for 15 min). After 2 hours, 10% citric acid and ethyl acetate were added. The organic phase was washed with NaHCO3 and brine, dried (MgSO4), and concentrated. Flash column chromatography of the residue (15% ethyl acetate/hexanes) gave 4 -(S)-4 -isopropyl-3-(2-naphthylacetyl)-2-oxazolidinone as a slightly yellow oil (0.91 g, 60%).

Aufarbeitung

  1. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-09a773d7c0d54027b85c272901318732
Quelldatensatz
uspto-grants-2000_04
Patentnummer
US06054470

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