Acetonitrile → HCID 12763412, compound

HRID 406515Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].C(#N)C.[C:10]([C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)#[N:11].Br[CH:20]([CH2:26][CH3:27])[C:21]([O:23][CH2:24][CH3:25])=[O:22]>O>[C:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH:20]([CH2:26][CH3:27])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:14][CH:13]=1)#[N:11]

Participants

Conditions

Temperature: 80 °C

Procedure

Potassium carbonate (14.5 g, 105 mmol) was added to an acetonitrile (80.0 mL) solution of 4-cyanophenol (5.00 g, 42.0 mmol) and ethyl 2-bromobutyrate (9.83 g, 50.4 mmol) at room temperature, and the mixture was stirred for 3 hours at 80° C. After the mixture was cooled to room temperature, water was added to the reaction mixture, and the mixture was subjected to extraction two times with ethyl acetate. The organic layer thus obtained was washed with saturated brine, and then was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→2:1, v/v). Thus, the title compound (9.79 g, yield: 100%) was obtained.

Workup

temperatureAfter the mixture was cooled to room temperature
extractionthe mixture was subjected to extraction two times with ethyl acetate
customThe organic layer thus obtained
washwas washed with saturated brine
dry with materialwas dried over anhydrous sodium sulfate
distillationThe solvent was distilled off under reduced pressure
customthe resulting residue was purified by silica gel column chromatography (hexane

Sources & evidence

ORD record: ord-c288c190e9d14a76b2d77616aa38ef85
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754112B2

Reaction notes

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