Propionyl chloride → HCID 69201683, compound

HRID 898351Notes

Reaction equation

HRID 898351 reaction equation
[C:1](Cl)(=[O:4])[CH2:2][CH3:3].[Cl-].[Al+3].[Cl-].[Cl-].[CH2:10]([C:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[O:19][C:18]=1[CH2:26][CH3:27])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(=S)=S>[CH2:10]([C:17]1[C:21]2[CH:22]=[CH:23][C:24]([C:1](=[O:4])[CH2:2][CH3:3])=[CH:25][C:20]=2[O:19][C:18]=1[CH2:26][CH3:27])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 62324Propionyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 69199322HCID 69199322, compound

Product 1

HCID 69201683HCID 69201683, compoundYield 4.2%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

Propionyl chloride (7.3 mL; 0.784 mol) was added dropwise to the mixture of Aluminum chloride (10.5 g; 0.784 mol), and 3-benzyl-2-ethyl-benzofuran (18.5 g; 0.784 mol) in carbon disulfide (50 mL) while stirring and cooling in an ice bath. The reaction mixture was then stirred at room temperature for 30 minutes then heated at reflux for 2 hours. The solvent was then evaporated and the residue was diluted with ether then poured into water. The organic phase was washed with water, dried over anhydrous magnesium sulfate and the solvent was evaporated. The residue was crystallized from ethyl acetate/hexane mixture to give the title compound (9.6 g) as a solid, mp: 86-87° C. Mass spectrum (ESI, [M+] m/z 292. 1HNMR (400 MHz, DMSO-d6): δ 1.08 (t, 3H, J=7.26 Hz), 1.24 (t, 3H, J=7.47 Hz), 2.88 (q, 2H, J=7.47 Hz), 2.04 (q, 2H, J=7.26 Hz), 4.02 (s, 2H), 7.16-7.19 (m,1H), 7.23-7.29 (m, 5H), 7.47 (d, 1H, J=8.09 Hz), 7.78 (dd, 1H, J=8.09, 1.45 Hz), 8.07 (d, 1H, J=1.45 Hz). Elemental Analysis for C20H20O2: Calculated: C, 82.16; H, 6.90 Found: C, 82.22; H, 7.01.

Workup

  1. temperaturecooling in an ice bath
  2. stirringThe reaction mixture was then stirred at room temperature for 30 minutes
  3. temperaturethen heated
  4. temperatureat reflux for 2 hours
  5. customThe solvent was then evaporated
  6. additionthe residue was diluted with ether
  7. additionthen poured into water
  8. washThe organic phase was washed with water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customthe solvent was evaporated
  11. customThe residue was crystallized from ethyl acetate/hexane mixture

Sources & evidence

ORD record
ord-8b00c77d4b1e46a0b920772cf5cf732d
Source dataset
uspto-grants-2008_04
Patent number
US07351726B2

Reaction notes

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