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 1453303Notes

Reaction equation

HRID 1453303 reaction equation
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]

Participants

4

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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 below), 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).

Workup

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

Sources & evidence

ORD record
ord-030e38ae65b64949ba15a196c04c1223
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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