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

HRID 1594682Notes

Reaction equation

HRID 1594682 reaction equation
[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]

Participants

5

Reactant 2

HCID 113932-Naphthaleneacetic acidHCID 65578Oxalyl chloride

Product 1

HCID 5881152-(2-Naphthyl)acetyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

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%).

Workup

  1. customthe solvent was evaporated

Sources & evidence

ORD record
ord-54932b00d0214719be95fdda76c92ae4
Source dataset
uspto-grants-2001_09
Patent number
US06284768B1

Reaction notes

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