Sodium hydride → (E)-3-(1H-Indol-7-yl)acrylonitrile

HRID 54526Notes

Reaction equation

HRID 54526 reaction equation
[H-].[Na+].[C:3]([CH2:5]P(=O)(OCC)OCC)#[N:4].[NH:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][C:21]=2[CH:23]=O)[CH:16]=[CH:15]1>O1CCCC1.C(OCC)(=O)C>[C:3](/[CH:5]=[CH:23]/[C:21]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:22]=1[NH:14][CH:15]=[CH:16]2)#[N:4]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 2734629Indole-7-carboxaldehyde

Product 1

HCID 19959103(E)-3-(1H-Indol-7-yl)acrylonitrile

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride, 60% dispersion in mineral oil (0.10 g, 2.5 mmol) is added in portions over 10 minutes to a stirred solution of diethyl cyanomethylphosphonate (0.44 g, 2.5 mmol) in tetrahydrofuran (10 ml) cooled in ice. The mixture is stirred for 15 minutes then a solution of 7-indole carboxaldehyde (0.30 g, 2.1 mmol) in tetrahydrofuran (2 ml) is added dropwise. The mixture is stirred for 30 minutes, diluted with ethyl acetate, washed with water, dried and evaporated. The residue is chromatographed on silica in ethyl acetate-hexane (1:3) to give the product.

Workup

  1. temperaturecooled in ice
  2. stirringThe mixture is stirred for 30 minutes
  3. washwashed with water
  4. customdried
  5. customevaporated
  6. customThe residue is chromatographed on silica in ethyl acetate-hexane (1:3)
  7. customto give the product

Sources & evidence

ORD record
ord-28339c89712f412387a749f34ff15d9b
Source dataset
uspto-grants-1997_04
Patent number
US05622969

Reaction notes

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