Chloroform → 4-Chloro-2,5-dimethyl-6-(2,4,6-trimethyl-phenoxy)pyridine

HRID 968027노트

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HRID 968027 반응식
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[OH:10].[H-].[Na+].Cl[C:14]1[C:19]([CH3:20])=[C:18]([Cl:21])[CH:17]=[C:16]([CH3:22])[N:15]=1.C(Cl)(Cl)Cl>CS(C)=O.CCCCCC>[Cl:21][C:18]1[CH:17]=[C:16]([CH3:22])[N:15]=[C:14]([O:10][C:3]2[C:4]([CH3:9])=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=2[CH3:1])[C:19]=1[CH3:20]

참가 물질

7

반응물 4

HCID 6212ChloroformHCID 106982,4,6-TrimethylphenolHCID 24758Sodium hydrideHCID 110843982,4-Dichloro-3,6-dimethylpyridine

생성물 1

HCID 99036754-Chloro-2,5-dimethyl-6-(2,4,6-trimethyl-phenoxy)pyridine

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 8058Hexane용매

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온도
130 °C

실험 절차

A solution of 2,4,6-trimethylphenol (405 mg, 3.31 mmol) in 2 ml of DMSO was treated with NaH (60% in oil, 180 mg, 4.5 mmol). After 5 min, 2,4-Dichloro-3,6-dimethyl-pyridine (528 mg, 3 mmol) was added. The mixture was heated in the oil bath of 130° C. for 6 hours. The mixture was quenched with water and extracted with EtOAc. The organic layer was dried and concentrated to give 812.5 mg of crude material with two regioisomers. After silica gel column chromatography using 1:1 of CHCl3:hexane as eluent, the title compound was isolated as white crystals (141 mg), mp 57-62° C.; high MS for C16H18ClNO: calc, 275.1072, found 275.70172; IR(KBr) 2951, 2920, 1592, 1564 cm−1; 1H NMR (CDCl3) δ 6.87 (s, 2H), 6.77 (s, 1H), 2.39 (s, 3H), 2.29 (s, 3H), 2.18 (s, 3H), 2.03 (s, 6H) ppm. The regiochemistry was determined by X-ray structural analysis of the undesired regioisomer, 2-chloro-3,6-dimethyl-4-(2,4,6-trimethyl-phenyoxy)-pyridine.

후처리

  1. customThe mixture was quenched with water
  2. extractionextracted with EtOAc
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. customto give 812.5 mg of crude material with two regioisomers

출처 및 근거

ORD 기록
ord-d69dee69bb0a406faddb0b7a4817909f
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06956047B1

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