Aluminum(III) Chloride → HCID 68492644, compound

HRID 1039160Notes

Reaction equation

HRID 1039160 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-8683e1ce82c64a99b11a09a29cfe4e93
Source dataset
uspto-grants-2013_10
Patent number
US08552039B2

Reaction notes

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