Sodium hydride → 2-(5-Methoxybenzo[b]furan-3-yl)acetonitrile
Reaction equation
[H-].[Na+].P([CH2:11][C:12]#[N:13])(OCC)(OCC)=O.[CH3:14][O:15][C:16]1[CH:25]=[CH:24][C:19]2[O:20][CH2:21][C:22](=O)[C:18]=2[CH:17]=1>C1COCC1>[CH3:14][O:15][C:16]1[CH:25]=[CH:24][C:19]2[O:20][CH:21]=[C:22]([CH2:11][C:12]#[N:13])[C:18]=2[CH:17]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -15 °C
Procedure
Under inert atmosphere, 83 mmol of sodium hydride are suspended in 100 ml of anhydrous THF. The temperature is cooled at -15° C. and 83 mmol (14.7 g) of (EtO)2POCH2CN in 50 ml of 1BF are dropply added. Then 55 mmol (9 g) of compound obtained in stage A in 100 ml of THF are dropwised at -15° C. The solution is stirred during 2 hours at that temperature before being hydrolysed. The mixture is extracted with ethyl acetate and the organic layers are washed with brine, dried over magnesium sulfate and concentrated. The title product is obtained after purification by chromatography on silica gel.
Workup
- customare dropwised at -15° C
- extractionThe mixture is extracted with ethyl acetate
- washthe organic layers are washed with brine
- dry with materialdried over magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-b515ed3bc03e42c583ddc8d774831303
- Source dataset
- uspto-grants-2000_06
- Patent number
- US06071946
Reaction notes
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