Acetic Acid → HCID 58261099, compound

HRID 868782Notes

Reaction equation

HRID 868782 reaction equation
[Br:1][C:2]1[S:3][C:4](Br)=[C:5]2[C:9](=[O:10])[N:8]([CH:11]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:7](=[O:28])[C:6]=12.C(O)C.C(O)(=O)C.Cl>[Zn].C(Cl)(Cl)Cl.CCCCCC>[Br:1][C:2]1[S:3][CH:4]=[C:5]2[C:9](=[O:10])[N:8]([CH:11]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:7](=[O:28])[C:6]=12

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 702EthanolHCID 58261070HCID 58261070, compound

Product 1

HCID 58261099HCID 58261099, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 6212ChloroformSolventHCID 8058HexaneSolvent

Procedure

1,3-Dibromo-5-(heptadecan-9-yl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione (9.43 g, 20.04 mmol) and zinc (1.31 g, 20.04 mmol) were placed in a 3 neck round-bottom flask equipped with a water condenser with ethanol (130 mL), acetic acid (40 mL) and 1 M HCl (2.5 mL). Mixture was refluxed for one hour after which an aliquot was taken for NMR analysis, which indicated reaction was complete. After cooling, the solution was filtered through fritted glass to eliminate remaining Zn particles and solvent was evaporated under vacuum. Product was obtained by silica chromatography, using a 100% hexane to 100% CHCl3 gradient.

Workup

  1. temperatureMixture was refluxed for one hour after which an aliquot
  2. customreaction
  3. temperatureAfter cooling
  4. filtrationthe solution was filtered through fritted glass
  5. customwas evaporated under vacuum
  6. customProduct was obtained by silica chromatography

Sources & evidence

ORD record
ord-c065daf79bde4d3885c7e72645238f38
Source dataset
uspto-grants-2015_03
Patent number
US08968885B2

Reaction notes

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