2-Thiophenecarboxaldehyde → 2-[1-(Ethoxy)ethoxy]-3-(2-thienyl)propenal

HRID 34729

Reaction equation

HRID 34729 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=O.[CH2:8]([O:10][CH:11]([O:13][CH2:14][CH:15]=[O:16])[CH3:12])[CH3:9]>C1(C)C=CC=CC=1>[CH2:8]([O:10][CH:11]([O:13][C:14](=[CH:6][C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)[CH:15]=[O:16])[CH3:12])[CH3:9]

Participants

4

Reactant 2

HCID 73642-ThiophenecarboxaldehydeHCID 13876797(1-Ethoxyethoxy)acetaldehyde

Product 1

HCID 537286552-[1-(Ethoxy)ethoxy]-3-(2-thienyl)propenalYield 20.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Except to use a reaction time of 36 hours at ambient temperature, and to use toluene as eluant on chromatography, thiophene-2-carbaldehyde (3.1 ml., 3.74 g., 0.083 mol) and 2-[1-(ethoxy)ethoxy)acetaldehyde (4.0 g., 0.030 mol) were converted to instant title product as a yellow solid 1.39 g., crystallized from hexane, 109 mg.; 1H-nmr: 1.14 (t, 3H), 1.52 (d, 3H), 3.75 (m, 2H), 6.01 (q, 1H), 6.99 (s, 1H), 7.15 (m, 1H), 7.53 (m, 2H), 9.40 (s, 1H).

Workup

  1. customa reaction time of 36 hours
  2. customat ambient temperature

Sources & evidence

ORD record
ord-f07449b67aed45059b187c568729655b
Source dataset
uspto-grants-1988_08
Patent number
US04762921

Linked notes

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