Tin tetrachloride → HCID 67255733, compound

HRID 2371055Notes

Reaction equation

HRID 2371055 reaction equation
[C:1]1([C:7]2[CH:15]=[CH:14][C:10]3[S:11][CH:12]=[CH:13][C:9]=3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:17](=[O:25])[CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].Cl[Sn](Cl)(Cl)Cl>C(Cl)Cl>[O:25]=[C:17]([C:13]1[C:9]2[CH:8]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH:15]=[CH:14][C:10]=2[S:11][CH:12]=1)[CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]

Participants

5

Reactant 3

HCID 24287Tin tetrachlorideHCID 84648Butanoic acid, 4-chloro-4-oxo-, ethyl esterHCID 57569240HCID 57569240, compound

Product 1

HCID 67255733HCID 67255733, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-phenylbenzo[b]thiophene (1.05 g, 5.0 mmol, 1 eq) in DCM (100 mL) at 0° C. was added ethyl 4-chloro-4-oxobutanoate (0.9 g, 21.4 mmol). The resulting mixture was stirred at 0° C. for 30 minutes. SnCl4 (2.3 mL, 6.0 mmol, 1.2 eq) was added and the mixture was stirred at room temperature overnight. The reaction mixture was quenched with aqueous HCl solution (50 mL, 3 M) and extracted with diethyl ether. The combined organic layers were dried over Na2SO4. After filtration and concentration, the crude product was purified by column chromatography to give the title compound.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. customThe reaction mixture was quenched with aqueous HCl solution (50 mL, 3 M)
  3. extractionextracted with diethyl ether
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationAfter filtration and concentration
  6. customthe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-f1c2909709da4f62861bbeae10a6f0ba
Source dataset
uspto-grants-2014_04
Patent number
US08710245B2

Reaction notes

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