Tin tetrachloride → HCID 10149127, compound

HRID 619618Notes

Reaction equation

HRID 619618 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][C:10]([CH3:16])([CH3:15])[CH2:11][C:12](Cl)=[O:13])=[CH:5][CH:4]=1.Cl[Sn](Cl)(Cl)Cl>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[C:7]2[C:6](=[CH:5][CH:4]=1)[S:9][C:10]([CH3:16])([CH3:15])[CH2:11][C:12]2=[O:13]

Participants

4

Reactant 2

HCID 24287Tin tetrachlorideHCID 22323720HCID 22323720, compound

Product 1

HCID 10149127HCID 10149127, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of the acyl chloride (Compound 217, 21.5 g, 83.2 mmol) in 250 mL of CH2Cl2 at 0° C. was added dropwise a solution of SnCl4 (21.7 g, 83.2 mmol) in 30 mL of CH2Cl2. After 2 hours the reaction was quenched by slow addition of 150 mL H2O. The organic layer was washed with 1M aqueous HCl, 5% aqueous NaOH, H2O, and finally saturated aqueous NaCl before being dried over MgSO4. Concentration under reduced pressure and vacuum distillation of the residual oil (Bulb-to-bulb, 125-135° C., 5 mm/Hg) afforded 14.48 g (78%) of the title compound as a pale-yellow oil. 1H NMR (300 MHz, CDCl3) δ: 7.62 (1H, d, J=2.9 Hz), 7.14 (1H, d, J=8.6 Hz), 7.03 (1H, dd, J=2.8, 8.3 Hz), 3.83 (3H, s), 2.87 (2H, s), 1.46 (6H, s).

Workup

  1. customAfter 2 hours the reaction was quenched by slow addition of 150 mL H2O
  2. washThe organic layer was washed with 1M aqueous HCl, 5% aqueous NaOH, H2O, and finally saturated aqueous NaCl
  3. dry with materialbefore being dried over MgSO4
  4. concentrationConcentration
  5. distillationunder reduced pressure and vacuum distillation of the residual oil (Bulb-to-bulb, 125-135° C., 5 mm/Hg)

Sources & evidence

ORD record
ord-84747276d33e4eb088913503e4a01c2e
Source dataset
uspto-grants-1999_09
Patent number
US05958954

Reaction notes

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