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

HRID 1005423

反応式

HRID 1005423 の反応式
[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]

参加物

5

反応物 2

HCID 113932-Naphthaleneacetic acidHCID 65578Oxalyl chloride

生成物 1

HCID 5881152-(2-Naphthyl)acetyl chloride

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  1. customthe solvent was evaporated

出典と根拠

ORDレコード
ord-09a773d7c0d54027b85c272901318732
出典データセット
uspto-grants-2000_04
特許番号
US06054470

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