Sodium Chloride → HCID 68827798, compound
Reaction equation
[C:1]1([CH2:7][C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:13][CH2:14][CH:15]=[CH2:16].[Cl-].[Na+]>CN(C=O)C.C(OCC)(=O)C>[CH2:13]([C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([CH2:3][CH2:2][CH:1]=[CH2:6])[C:8]#[N:9])[CH2:14][CH2:15][CH3:16]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 2-phenylacetonitrile (1 mL) in DMF (1.0 mL) at 0° C. was added sodium hydride (95% oil dispersion, 547 mg) and the resulting suspension was stirred at 0° C. for 10 min. 4-Bromobut-1-ene (2.2 mL) was added, and the reaction mixture was stirred at room temperature for 2 h. Saturated sodium chloride was added followed by ethyl acetate, the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and filtered, and the filtrate was evaporated in vacuo. The residue was purified by silica gel flash chromatography eluting with 10% ethyl acetate/90% hexanes to give the title compound as an oil (773 mg). 1H NMR (400 MHz, CDCl3) δ 1.8-2.3 (8H, m), 4.95 (4H, m), 5.73 (2H, m), and 7.31 (5H, m).
Workup
- stirringthe reaction mixture was stirred at room temperature for 2 h
- extractionthe aqueous layer was extracted with ethyl acetate
- dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
- filtrationfiltered
- customthe filtrate was evaporated in vacuo
- customThe residue was purified by silica gel flash chromatography
- washeluting with 10% ethyl acetate/90% hexanes
Sources & evidence
- ORD record
- ord-6ae3ebdf9f574a7c830ba35a6c506e39
- Source dataset
- uspto-grants-2009_02
- Patent number
- US07494986B2
Reaction notes
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