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

HRID 1005423

반응식

HRID 1005423 반응식
[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]

참가 물질

5

반응물 2

HCID 113932-Naphthaleneacetic acidHCID 65578Oxalyl chloride

생성물 1

HCID 5881152-(2-Naphthyl)acetyl chloride

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  1. customthe solvent was evaporated

출처 및 근거

ORD 기록
ord-09a773d7c0d54027b85c272901318732
출처 데이터셋
uspto-grants-2000_04
특허 번호
US06054470

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