Aluminium lithium hydride → HCID 59334486, compound

HRID 1639835Notes

Reaction equation

HRID 1639835 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[C:10]([C:11](OC)=[O:12])=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1.C(OCC)(=O)C.O.[OH-].[Na+].Cl>[CH3:1][C:2]1[S:3][C:4]2[C:10]([CH2:11][OH:12])=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

8

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 45077175Methyl 2-methyl-7-benzothiazolecarboxylate

Product 1

HCID 59334486HCID 59334486, compoundYield 92%

Reagents, catalysts & solvents 5

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

Under nitrogen atmosphere, to a solution of methyl 2-methyl-1,3-benzothiazole-7-carboxylate (6.00 g, 29.0 mmol) in tetrahydrofuran (150 mL) was added lithium aluminum hydride (1.18 g, 34.7 mmol) at 0° C., and the mixture was stirred at room temperature for 1 hr. The reaction mixture was diluted with ethyl acetate and water, 1 M aqueous sodium hydroxide solution (10 mL) and 2 M hydrochloric acid (10 mL) were added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/1) to give the title compound (4.78 g, yield 92%).

Workup

  1. additionwere added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/1)

Sources & evidence

ORD record
ord-d824e62b529a4cb195bd1230e60a96b1
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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