Distannoxane, 1,1,3,3-tetrabutyl-1,3-dichloro- → 3-chloro-6-[2-(3-chloro-4-methoxyphenyl)ethyl]6-cyclopentyl-4-hydroxy-5,6-dihydro-2H-pyran-2-one

HRID 1453272

반응식

HRID 1453272 반응식
C[O:2][C:3](=[O:27])[CH:4]([Cl:26])[C:5](=[O:25])[CH2:6][C:7]([CH:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1)(O)[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([Cl:18])[CH:11]=1.CCCC[Sn](Cl)(O[Sn](Cl)(CCCC)CCCC)CCCC>C1(C)C=CC=CC=1>[Cl:26][C:4]1[C:3](=[O:2])[O:27][C:7]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([Cl:18])[CH:11]=2)([CH:20]2[CH2:21][CH2:22][CH2:23][CH2:24]2)[CH2:6][C:5]=1[OH:25]

참가 물질

4

반응물 2

HCID 16682755Distannoxane, 1,1,3,3-tetrabutyl-1,3-dichloro-HCID 210622722-Chloro-7-(3-chloro-4-methoxy-phenyl)-5-cyclopentyl-5-hydroxy-3-oxo-heptanoic acid methyl ester

생성물 1

HCID 547203223-chloro-6-[2-(3-chloro-4-methoxyphenyl)ethyl]6-cyclopentyl-4-hydroxy-5,6-dihydro-2H-pyran-2-one수율 75%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A solution of 2-Chloro-7-(3-chloro-4-methoxy-phenyl)-5-cyclopentyl-5-hydroxy-3-oxo-heptanoic acid methyl ester (2.33 g, 5.6 mmol, from Step 1), and bis(dibutylchlorotin)oxide (1.38 g, 2.5 mmol), dissolved in toluene (18 mL) were heated at reflux for 30 mins. The resulting mixture was concentrated and purified by silica gel chromatography to give the title compound (1.57 g, 75% yield, two Steps). 1H NMR (CDCl3): δ 1.36-1.79 (br m, 8H), 2.02 (m, 2H), 2.41 (m, 1H), 2.65 (m, 3H), 2.89 (d, 1H, J=17.7 Hz), 3.88 (s, 3H), 6.47 (br s, 1H), 6.85 (d, 1H, J=8.4 Hz), 7.01 (dd, 1H, J=8.4, 2.1 Hz), 7.16 (d, 1H, J=2.1 Hz).

후처리

  1. temperaturewere heated
  2. temperatureat reflux for 30 mins
  3. concentrationThe resulting mixture was concentrated
  4. custompurified by silica gel chromatography

출처 및 근거

ORD 기록
ord-25dc1c8462614255b4e693a0c28bf551
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07473790B2

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