2-Thiophenecarboxaldehyde → HCID 21435162, compound

HRID 2398296Notes

Reaction equation

HRID 2398296 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1C=O.C(OP([CH:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:24]#[N:25])[CH3:17])(=O)OCC)C.[CH3:26][O-].[Na+]>CN(C)C=O>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:24]#[N:25])[CH:17]=[CH2:26]

Participants

5

Reactant 3

HCID 73642-ThiophenecarboxaldehydeHCID 10942334Sodium MethoxideHCID 54217811HCID 54217811, compound

Product 1

HCID 21435162HCID 21435162, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 73.0 g of 2-thiophenaldehyde and 170 g of diethyl-1-(o-cyanophenyl)ethylphosphonate in 800 ml of anhydrous dimethyl formamide was added dropwise in a nitrogen atmosphere at 20°-30°to a suspension of 39.0 g of sodium methylate in 500 ml of anhydrous dimethyl formamide. The mixture was further stirred for 1 hour at 40°, cooled to 10°-15° and treated with ca. 5 1 of icewater. Working up gave 2-[1-(2-thienyl)-2-propenyl]benzonitrile, B.Pt. (0.1 to 0.2 mm Hg) = 200°-210° .

Workup

  1. temperaturecooled to 10°-15°
  2. additiontreated with ca. 5 1 of icewater

Sources & evidence

ORD record
ord-184f72439db5471d8efec10845114af0
Source dataset
uspto-grants-1977_05
Patent number
US04024266

Reaction notes

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