Pyridine → HCID 58083713, 화합물

HRID 558029

반응식

HRID 558029 반응식
[CH3:1][O:2][C:3](=[O:17])[CH:4]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([OH:16])[CH:12]=2)[CH:7]=1)[CH3:5].N1C=CC=CC=1.[Br:24][CH2:25][C:26](Cl)=[O:27]>ClCCl>[CH3:1][O:2][C:3](=[O:17])[CH:4]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:16][C:26](=[O:27])[CH2:25][Br:24])[CH:12]=2)[CH:7]=1)[CH3:5]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 89602Bromoacetyl chlorideHCID 5988972-(6-Hydroxy-naphthalen-2-yl)-propionic acid methyl ester

생성물 1

HCID 58083713HCID 58083713, 화합물수율 45.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 2-(6-hydroxy-naphthalen-2-yl)-propionic acid methyl ester (20 grams) and pyridine (10.3 grams) in dichloromethane (200 ml) maintained at 0-5° C. under N2 atmosphere was added dropwise bromoacetyl chloride (19.6 grams). The reaction was stirred at the same temperature for one hour. The reaction mixture was washed with water (500 ml) and 5% solution of sodium carbonate followed by drying over sodium sulphate and distillation to get crude compound, which was purified by column chromatography using hexane as eluant to get pure 2-[6-(2-bromo-acetoxy)-naphthalen-2-yl]-propionic acid methyl ester (14 grams) as a dark brown syrup. The pure product was characterized using 1H NMR spectroscopy in CDCl3 δ 1.55 (d, 3H, CH3), 3.65 (s, 3H, Ester), 3.82 (q, 1H, CH), 4.08 (s, 2H, OCH2) 7.20 (dd, 1H, Ar), 7.4 (dd, 1H, Ar), 7.57 (d, 1H, Ar), 7.72 (d, 1H, Ar), 7.78 (d, 1H, Ar), 7.84 (d, 1H, Ar).

후처리

  1. washThe reaction mixture was washed with water (500 ml) and 5% solution of sodium carbonate
  2. dry with materialby drying over sodium sulphate and distillation
  3. customto get crude compound, which
  4. customwas purified by column chromatography

출처 및 근거

ORD 기록
ord-3fefca0c207647a582ef51a034ddd878
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08062653B2

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