Bis(tributyltin) oxide → HCID 86645806, compound

HRID 1695170Notes

Reaction equation

HRID 1695170 reaction equation
[C:1]([O:5][C:6](=[O:29])[C@H:7]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C@@H:8]([O:15]C(=O)C1C=CC=CC=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])([CH3:4])([CH3:3])[CH3:2].CCCC[Sn](O[Sn](CCCC)(CCCC)CCCC)(CCCC)CCCC>C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:29])[C@H:7]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C@@H:8]([OH:15])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 16682746Bis(tributyltin) oxideHCID 67274648HCID 67274648, compound

Product 1

HCID 86645806HCID 86645806, compoundYield 54.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The (2R,3S)-3-benzoyloxy-2-pentylnonanoic acid t-butyl ester (1.24 g, 3.06 mmol) obtained in Production Example C-7-1 was dissolved in anhydrous toluene (4 ml), and then tributyltin oxide (2.34 g, 3.92 mmol) was added thereto to be refluxed with heating. Then, 39 hours later, distilled water was added to the reaction mixture, and extracted 3 times with diethyl ether. The resulting organic layer was dried with anhydrous magnesium sulfate, filtered, and condensed. The obtained residue was purified by column chromatography (silica gel: 30 g, n-hexane/ethyl acetate=20/1), and the target compound (501 mg, 54%) was obtained.

Workup

  1. temperatureto be refluxed
  2. temperaturewith heating
  3. distillationThen, 39 hours later, distilled water
  4. additionwas added to the reaction mixture
  5. extractionextracted 3 times with diethyl ether
  6. dry with materialThe resulting organic layer was dried with anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customcondensed
  9. customThe obtained residue was purified by column chromatography (silica gel: 30 g, n-hexane/ethyl acetate=20/1)

Sources & evidence

ORD record
ord-64bcbed5c833460ca7155c72222bb62a
Source dataset
uspto-grants-2012_04
Patent number
US08163713B2

Reaction notes

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