Ammonium Chloride → 5-[4-(4-Ethoxy-2,3-difluorophenoxymethyl)cyclohexyl]-2-trimethylsilanylethynyltetrahydropyran-2-ol

HRID 605455Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 605455
[CH3:1][Si:2]([C:5]#[CH:6])([CH3:4])[CH3:3].C([Li])CCC.[CH2:12]([O:14][C:15]1[CH:35]=[CH:34][C:18]([O:19][CH2:20][CH:21]2[CH2:26][CH2:25][CH:24]([CH:27]3[CH2:32][O:31][C:30](=[O:33])[CH2:29][CH2:28]3)[CH2:23][CH2:22]2)=[C:17]([F:36])[C:16]=1[F:37])[CH3:13].[Cl-].[NH4+]>C1COCC1.CCCCCC>[CH2:12]([O:14][C:15]1[CH:35]=[CH:34][C:18]([O:19][CH2:20][CH:21]2[CH2:26][CH2:25][CH:24]([CH:27]3[CH2:32][O:31][C:30]([C:6]#[C:5][Si:2]([CH3:4])([CH3:3])[CH3:1])([OH:33])[CH2:29][CH2:28]3)[CH2:23][CH2:22]2)=[C:17]([F:36])[C:16]=1[F:37])[CH3:13]

Komponenten

7

Edukt 4

HCID 25517Ammonium ChlorideHCID 66111TrimethylsilylacetyleneHCID 668767205-[4-(4-Ethoxy2,3-difluorophenoxymethyl)cyclohexyl]tetrahydropyran-2-oneHCID 178418339Butyllithium

Produkt 1

HCID 668769855-[4-(4-Ethoxy-2,3-difluorophenoxymethyl)cyclohexyl]-2-trimethylsilanylethynyltetrahydropyran-2-olAusbeute 92,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

2.55 g of trimethylsilylacetylene was dissolved in 20 mL THF, and then 15.7 mL of a 1.66 M hexane solution of n-butyllithium was added dropwise thereto at −70° C., followed by stirring at that temperature for 1 hour. To the resulting solution, a solution containing 9.12 g of 5-[4-(4-ethoxy-2,3-difluorophenoxymethyl)cyclohexyl]tetrahydropyran-2-one obtained in the twelfth step of Example 1 dissolved in 30 mL of THF was added dropwise at −70° C., followed by stirring at that temperature for 1 hour, and then the temperature of the solution was gradually increased to room temperature. The reaction product was poured into 50 mL of a saturated ammonium chloride aqueous solution, and the mixture was extracted with diethyl ether. The organic layer was washed with water and concentrated under reduced pressure. The resulting brown residue was purified by silica gel column chromatography to provide 10.7 g of 5-[4-(4-ethoxy-2,3-difluorophenoxymethyl)cyclohexyl]-2-trimethylsilanylethynyltetrahydropyran-2-ol as a brown solid.

Aufarbeitung

  1. customat −70° C.
  2. customobtained in the twelfth step of Example 1
  3. additionwas added dropwise at −70° C.
  4. stirringby stirring at that temperature for 1 hour
  5. extractionthe mixture was extracted with diethyl ether
  6. washThe organic layer was washed with water
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting brown residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-1efc1bba8bdc4dba93b79a9cbb07095c
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07914862B2

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