Triethylamine → 1-(Thiophen-2-yl)prop-2-en-1-one

HRID 709391Notes

Reaction equation

HRID 709391 reaction equation
Cl[CH2:2][CH2:3][C:4]([C:6]1[S:7][CH:8]=[CH:9][CH:10]=1)=[O:5].C(N(CC)CC)C>C(OCC)C>[S:7]1[CH:8]=[CH:9][CH:10]=[C:6]1[C:4](=[O:5])[CH:3]=[CH2:2]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 75678553-Chloro-1-(2-thienyl)-1-propanone

Product 1

HCID 101032411-(Thiophen-2-yl)prop-2-en-1-oneYield 99%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

12 g of 3-chloro-1-(thiophen-2-yl)propan-1-one) prepared in Example 1a are solubilized in ethyl ether (180 mL). Triethylamine (10.2 g; 100 mmoles) is added at room temperature. The mixture is left under stirring for 60 hours, then washed with a HCl 10% solution and extracted with ethyl ether (2×20 mL). The organic phase is anhydrified with sodium sulphate, filtered and the solvent removed under vacuum. 9.4 g of 1-(thiophen-2-yl)-prop-2-en-1-one are obtained (yellow oil, yield 99%). Rf=0.74 (ligroin/ethyl acetate 8/2 volume/volume); 1H NMR (CDCl3) δ (ppm): 7.76 (m, 1H, ArH), 7.68 (m, 1H, ArH), 7.10 (m, 2H, ArH), 6.49 (m, 1H, CH2), 5.87 (m, 1H, CH2); 13C NMR (CDCl3) δ (ppm): 182.4, 144.6, 134.4, 132.5, 131.9, 129.4, 128.3; FT-IR (film) νmax: 3094.5, 1645.1, 1409.7, 1240.2, 850.4, 716 cm−1.

Workup

  1. waitThe mixture is left
  2. washwashed with a HCl 10% solution
  3. extractionextracted with ethyl ether (2×20 mL)
  4. filtrationfiltered
  5. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-de46ba919d174e45b7387c4ec961a88b
Source dataset
uspto-grants-2015_11
Patent number
US09181196B2

Reaction notes

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