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

反応式

HRID 1453272 の反応式
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]

参加物

4

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-25dc1c8462614255b4e693a0c28bf551
出典データセット
uspto-grants-2009_01
特許番号
US07473790B2

関連ノート

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