Aluminium lithium hydride → HCID 86645040, compound

HRID 1473988Notes

Reaction equation

HRID 1473988 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([C:14](OCC)=[O:15])[N:13]=2)=[CH:4][C:3]=1[O:19][CH2:20][CH:21]=[C:22]([CH3:24])[CH3:23].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH2:14][OH:15])[N:13]=2)=[CH:4][C:3]=1[O:19][CH2:20][CH:21]=[C:22]([CH3:24])[CH3:23]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86645038HCID 86645038, compound

Product 1

HCID 86645040HCID 86645040, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of ethyl 2-(4-methyl-3-(3-methylbut-2-enyloxy)phenylamino)thiazole-4-carboxylate (52 mg, 0.15 mmol) in anhydrous THF (1 mL) was added to a suspension of LiAla4 (9 mg, 0.22 mmol) in dry THF (1 mL) at 0° C. under nitrogen atmosphere. After 1 h 30 min, additional LiAlH4 (9 mg, 0.22 mmol) was added. After 1 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 obtain the title compound (27 mg, 59% 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-31468769081f4fa7bf9bc4c2b20e1868
Source dataset
uspto-grants-2015_04
Patent number
US09018209B2

Reaction notes

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