Aluminium lithium hydride → HCID 15956114, compound

HRID 1473989Notes

Reaction equation

HRID 1473989 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[S:11][CH:12]=[C:13]([C:15](OCC)=[O:16])[N:14]=2)=[CH:5][C:4]=1[O:20][CH2:21][CH:22]=[C:23]([CH3:25])[CH3:24].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[S:11][CH:12]=[C:13]([CH2:15][OH:16])[N:14]=2)=[CH:5][C:4]=1[O:20][CH2:21][CH:22]=[C:23]([CH3:25])[CH3:24]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86645039HCID 86645039, compound

Product 1

HCID 15956114HCID 15956114, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of ethyl 2-(4-methoxy-3-(3-methylbut-2-enyloxy)phenylamino)thiazole-4-carboxylate (67 mg, 0.18 mmol) in anhydrous THF (1 mL) was added to a suspension of LiAlH4 (14 mg, 0.37 mmol) in dry THF (1 mL) at 0° C. under nitrogen atmosphere. After 3 h, the reaction mixture was quenched with H2O, filtrated, dried over MgSO4 and concentrated. The crude product was purified by flash chromatography on silica gel (hexane:EtOAc 1/1) to give the title compound (30 mg, 50% yield).

Workup

  1. customthe reaction mixture was quenched with H2O
  2. filtrationfiltrated
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product was purified by flash chromatography on silica gel (hexane:EtOAc 1/1)

Sources & evidence

ORD record
ord-3a133b1f9ae143b29a5a0986193a8732
Source dataset
uspto-grants-2015_04
Patent number
US09018209B2

Reaction notes

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