Trimethylaluminum → HCID 68518935, compound

HRID 1948355Notes

Reaction equation

HRID 1948355 reaction equation
[CH3:1][Al](C)C.[C:5]([C:8]1[N:9]=[C:10]([Cl:17])[S:11][C:12]=1[C:13]([O:15][CH3:16])=[O:14])(=[O:7])[CH3:6]>C1(C)C=CC=CC=1.C(Cl)Cl>[Cl:17][C:10]1[S:11][C:12]([C:13]([O:15][CH3:16])=[O:14])=[C:8]([C:5]([OH:7])([CH3:1])[CH3:6])[N:9]=1

Participants

5

Reactant 2

HCID 16682925TrimethylaluminumHCID 59208338HCID 59208338, compound2×

Product 1

HCID 68518935HCID 68518935, compoundYield 27.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 5.6 ml (11.2 mmol) 2N AlMe3 in toluene was added to a dry ice-acetone bath of 1.14 g (5.2 mol) of methyl 4-acetyl-2-chloro-1,3-thiazole-5-carboxylate (Intermediate 212) in 20 ml dry CH2Cl2. The mixture was allowed to warm to room temperature slowly before being quenched with MeOH. After stirring at room temperature overnight, the mixture was diluted with 1N HCl and stirred 15 min before being diluted with water and extracted twice with EtOAc. The EtOAc was washed with brine, dried (MgSO4) and concentrated to give an oil that was purified by chromatography (50% hexanes in CH2Cl2 with gradient elution to 100% CH2Cl2) affording 720 mg of product as an oil. NMR (CDCl3): 1.5 (s, 6H), 3.8 (s, 3H), 5.7 (s, broad, 1H).

Workup

  1. custombefore being quenched with MeOH
  2. additionthe mixture was diluted with 1N HCl
  3. stirringstirred 15 min
  4. additionbefore being diluted with water
  5. extractionextracted twice with EtOAc
  6. washThe EtOAc was washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customto give an oil that
  10. customwas purified by chromatography (50% hexanes in CH2Cl2 with gradient elution to 100% CH2Cl2)

Sources & evidence

ORD record
ord-d92677b07e3b455192db71a1097d99fa
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

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