Tributyl(prop-1-yn-1-yl)stannane → Rac-2-(2,6-dimethyl-4-prop-1-ynylphenyl)-4-(tetrahydropyran-4-ylmethyl)cyclopentane-1,3-dione

HRID 514204

Reaktionsgleichung

Reaktionsgleichung von HRID 514204
Br[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[C:13](=[O:14])[CH:12]([CH2:15][CH:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[CH2:11][C:10]=2[O:22]C(=O)C(C)(C)C)=[C:4]([CH3:29])[CH:3]=1.[CH2:30]([Sn](CCCC)(CCCC)C#CC)[CH2:31][CH2:32]C>C1(C)C=CC=CC=1>[CH3:8][C:6]1[CH:7]=[C:2]([C:30]#[C:31][CH3:32])[CH:3]=[C:4]([CH3:29])[C:5]=1[CH:9]1[C:13](=[O:14])[CH:12]([CH2:15][CH:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[CH2:11][C:10]1=[O:22]

Komponenten

4

Edukt 2

HCID 2733165Tributyl(prop-1-yn-1-yl)stannaneHCID 58481557Rac-2,2-dimethylpropionic acid 2-(4-bromo-2,6-dimethylphenyl)-3-oxo-4-(tetrahydropyran-4-ylmethyl)cyclopent-1-enyl ester

Produkt 1

HCID 89601088Rac-2-(2,6-dimethyl-4-prop-1-ynylphenyl)-4-(tetrahydropyran-4-ylmethyl)cyclopentane-1,3-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

To a degassed solution of rac-2,2-dimethylpropionic acid 2-(4-bromo-2,6-dimethylphenyl)-3-oxo-4-(tetrahydropyran-4-ylmethyl)cyclopent-1-enyl ester (0.20 g, 0.43 mmol) in toluene (4 ml) under a nitrogen atmosphere is added tributyl(1-propynyl)tin (0.39 ml, 1.29 mmol) and tetrakistriphenylphosphine palladium(0) (0.10 g, 0.086 mmol). The reaction mixture is then heated at 130°C. under microwave irradiation for 45 minutes, followed by quenching with distilled water (20 ml) and extraction with ethyl acetate (50 ml×2). The combined organic fractions are washed with water, brine, dried over sodium sulphate, filtered and the filtrate is concentrated in vacuo. The residue is then dissolved in methanol (1.0 ml) and 2N sodium hydroxide solution (0.5 ml) is added followed by stirring at 25°C. for 3 hours. The solvent is evaporated in vacuo and the crude product is diluted with distilled water, acidified with 2N hydrochloric acid then extracted with ethyl acetate (50 ml×3). The combined organic fractions are washed with water, brine, dried over sodium sulphate, filtered and the filtrate is concentrated in vacuo to afford rac-2-(2,6-dimethyl-4-prop-1-ynylphenyl)-4-(tetrahydropyran-4-ylmethyl)cyclopentane-1,3-dione.

Aufarbeitung

  1. customby quenching with distilled water (20 ml) and extraction with ethyl acetate (50 ml×2)
  2. washThe combined organic fractions are washed with water, brine
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. concentrationthe filtrate is concentrated in vacuo
  6. dissolutionThe residue is then dissolved in methanol (1.0 ml)
  7. addition2N sodium hydroxide solution (0.5 ml) is added
  8. customThe solvent is evaporated in vacuo
  9. additionthe crude product is diluted with distilled water
  10. extractionthen extracted with ethyl acetate (50 ml×3)
  11. washThe combined organic fractions are washed with water, brine
  12. dry with materialdried over sodium sulphate
  13. filtrationfiltered
  14. concentrationthe filtrate is concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f2f5ec61b35a44d3a9a35bef2992a2d8
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09107415B2

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