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Sodium hydride → 2-(5-Methoxybenzo[b]furan-3-yl)acetonitrile

HRID 1420782
Notes
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Reaction equation

HRID 1420782 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]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 3466085-Methoxybenzofuran-3(2H)-one

Product 1

HCID 156187282-(5-Methoxybenzo[b]furan-3-yl)acetonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

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

  1. customare dropwised at -15° C
  2. extractionThe mixture is extracted with ethyl acetate
  3. washthe organic layers are washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b515ed3bc03e42c583ddc8d774831303
Source dataset
uspto-grants-2000_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06071946

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes