Ammonium Chloride → [1-Cyano-2-(tetrahydro-pyran-4-yl)-hex-5-enyl]-phosphonic acid diethyl ester

To a stirred solution of the oil isolated in Step A (51.26 g, 188 mmol) and CuI (1.00 g) in THF (200 mL) at −30° C., 3-butenylmagnesium bromide in THF (0.5 M, 394 mL, 197 mmol) was added slowly. The reaction mixture was stirred at room temperature overnight. Aqueous saturated ammonium chloride solution (300 mL) was then added. The reaction mixture was stirred 30 min at room temperature and then was extracted with ethyl acetate (400 mL) once. The organic solution was washed with saturated ammonium chloride solution three times, with brine one time and then was dried over magnesium sulfate. The reaction mixture was then filtered and concentrated to yield a residue. The residue was purified by Kugelrohr distillation to yield [1-cyano-2-(tetrahydro-pyran-4-yl)-hex-5-enyl]-phosphonic acid diethyl ester as a colorless oil.

1. stirringThe reaction mixture was stirred 30 min at room temperature
2. extractionwas extracted with ethyl acetate (400 mL) once
3. washThe organic solution was washed with saturated ammonium chloride solution three times, with brine one time
4. dry with materialwas dried over magnesium sulfate
5. filtrationThe reaction mixture was then filtered
6. concentrationconcentrated
7. customto yield a residue
8. distillationThe residue was purified by Kugelrohr distillation

ORD-Eintrag

ord-6156d660a8354fb295a07f3b20061690

Quelldatensatz

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07868022B2