3-(Cyclopentyloxy)-4-methoxyphenylacetonitrile → HCID 9857013, compound

HRID 1992728Notes

Reaction equation

[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH2:15][C:16]#[N:17])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.C[Si](C)(C)N[Si](C)(C)C.[Li]>O1CCCC1.[Cl-].[NH4+]>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3([C:16]#[N:17])[CH2:3][CH:2]=[CH:1][CH2:5]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

Conditions

Temperature: -78 °C

Procedure

2-(3-Cyclopentyloxy-4-methoxyphenyl)ethane nitrile (4.0 g) was dissolved in tetrahydrofuran (75 ml) under argon atmosphere, and a tetrahydrofuran solution (40.4 ml) of 1.0 M lithium hexamethyldisilazane was added dropwise thereto at −78° C., followed by stirring at −78° C. for 1 hour. The reaction mixture was diluted with a saturated aqueous ammonium chloride solution, and extracted with ethyl acetate. The extract was washed with water and saturated saline in this order, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:1) to thereby obtain the title compound (3.05 g) having the following physical properties.

Workup

customat −78° C.
extractionextracted with ethyl acetate
washThe extract was washed with water and saturated saline in this order
dry with materialdried with anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:1)

Sources & evidence

ORD record: ord-498cc4dfcf7441d5b04419c99f8dac2a
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07649095B2

Reaction notes

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