Aluminum(III) Chloride → HCID 68492644, compound

HRID 1616546Notes

Reaction equation

HRID 1616546 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][O:6][C:7](=[O:30])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]1[S:15][C:16]([C:19]2[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=2[O:26]C(C)C)=[CH:17][N:18]=1>C(Cl)Cl>[CH3:5][O:6][C:7](=[O:30])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]1[S:15][C:16]([C:19]2[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=2[OH:26])=[CH:17][N:18]=1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 59167803HCID 59167803, compound

Product 1

HCID 68492644HCID 68492644, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add aluminum(III) chloride (6.67 g, 50 mmol) portionwise to a solution of 7-[5-(5-chloro-2-isopropoxyphenyl)thiazol-2-yl]heptanoic acid methyl ester (9.90 g, 25 mmol) in methylene chloride (300 mL) at 0° C. under nitrogen. Slowly warm the mixture to room temperature and stir for an additional 30 minutes. Cool the mixture to 0° C., treat with saturated aqueous sodium sulfate Na2SO4 (150 ml), and stir for 1 hour. Remove the solvent under reduced pressure, dilute the residue with ethyl acetate (300 mL), wash with water (100 mL) and brine (100 mL), and dry over sodium sulfate. Remove the solvent under reduced pressure and purify the residue by flash column chromatography on silica gel, eluting with ethyl acetate/hexanes (1:9 to 1:1), to afford 7-[5-(5-chloro-2-hydroxyphenyl)thiazol-2-yl]heptanoic acid methyl ester (5.67 g, 64%).

Workup

  1. temperatureCool the mixture to 0° C.
  2. stirringstir for 1 hour
  3. customRemove the solvent under reduced pressure
  4. additiondilute the residue with ethyl acetate (300 mL)
  5. washwash with water (100 mL) and brine (100 mL)
  6. dry with materialdry over sodium sulfate
  7. customRemove the solvent under reduced pressure
  8. custompurify the residue by flash column chromatography on silica gel
  9. washeluting with ethyl acetate/hexanes (1:9 to 1:1)

Sources & evidence

ORD record
ord-a38495cb310a49d4a1725fcf4cc61edb
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Reaction notes

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