3-Thiophenecarboxaldehyde → HCID 123554834, compound

HRID 709393Notes

Reaction equation

HRID 709393 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH:6]=O)=[CH:2]1.CC(C)([O-:11])C.[K+].CS(C)=O.[CH2:18]1[CH2:22][O:21][CH2:20][CH2:19]1>>[S:1]1[CH:5]=[CH:4][C:3]([CH:6]=[CH:22][CH2:18][CH2:19][C:20]([OH:11])=[O:21])=[CH:2]1

Participants

4

Reactant 3

HCID 681353-ThiophenecarboxaldehydeHCID 21830753dimethylsulfoxide THFHCID 23665647Potassium tert-butoxide

Product 1

HCID 123554834HCID 123554834, compoundYield 70%

Procedure

To a suspension in DMSO/THF 1:1 volume/volume (26 mL) of 3-thiophencarboxaldehyde (2.0 g; 18 mmoles) and 2-(carboxyethyl) (triphenyl)phosphonium bromide (8.9 g; 21 mmoles) 5.3 g of potassium t-butoxide are added. The reaction mixture is left under stirring for 2 hours at room temperature. Then the organic phase is washed with water (20 mL) and extracted with chloroform (2×20 mL). The solvent is removed and the aqueous phase is acidified with concentrated HCl and extracted with chloroform (2×20 mL). The organic phase is recovered and washed with water and dried with sodium sulphate. After filtration, the organic phase is concentrated under vacuum. The obtained residue is purified by chromatography on silica gel by using as eluent a ligroin/ethyl acetate 1:1 volume/volume mixture. 2.3 g of a mixture of the two cis and trans diastereoisomers of the 5-(thiophen-3-il)-pent-4-enoic acid are obtained (yield 70%). Rf=0.35 (ligroin/ethyl acetate 6/4 volume/volume); 1H NMR (CDCl3) δ (ppm): 7.29 (m, 1H, ArH), 7.23 (m, 1H, ArH), 7.18 (m, 2H, ArH), 7.09 (m, 2H, ArH), 6.44 (m, 2H, CH), 6.06 (m, 1H, CH), 5.57 (m, 2H, CH), 2.68 (m, 2H, CH2), 2.52 (m, 6H, CH2); 13C NMR (CDCl3) δ (ppm): 179.2, 179.1, 139.9, 138.2, 128.9, 128.5, 127.9, 125.9, 125.5, 125.2, 124.9, 124.5, 123.1, 121.2, 33.9, 33.8, 27.8, 24.2; FT-IR (film) νmax: 3098.1, 2923.5, 1693.2, 1410.6, 1267.7, 1242.6, 1206.6, 1155.3, 966.1, 755.4 cm−1.

Workup

  1. waitThe reaction mixture is left
  2. washThen the organic phase is washed with water (20 mL)
  3. extractionextracted with chloroform (2×20 mL)
  4. customThe solvent is removed
  5. extractionextracted with chloroform (2×20 mL)
  6. customThe organic phase is recovered
  7. washwashed with water
  8. dry with materialdried with sodium sulphate
  9. filtrationAfter filtration
  10. concentrationthe organic phase is concentrated under vacuum
  11. customThe obtained residue is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-2c394c849d11487ba5832f8b82adefd2
Source dataset
uspto-grants-2015_11
Patent number
US09181196B2

Reaction notes

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