Aluminium lithium hydride → HCID 58934092, compound

HRID 490709Notes

Reaction equation

HRID 490709 reaction equation
C[O:2][C:3](=O)[CH2:4][C:5]1[N:6]=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)[S:8][C:9]=1[CH2:10][CH2:11][CH3:12].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:10]([C:9]1[S:8][C:7]([C:13]2[CH:14]=[CH:15][C:16]([C:19]([F:20])([F:22])[F:21])=[CH:17][CH:18]=2)=[N:6][C:5]=1[CH2:4][CH2:3][OH:2])[CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 69055671HCID 69055671, compound

Product 1

HCID 58934092HCID 58934092, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

[[5-Propyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-acetic acid methyl ester (8.66 g, 24.2 mmol) is dissolved into anhydrous tetrahydrofuran (THF) (100 mL) and then cooled to 0° C. with stirring. Lithium aluminum hydride (24.2 mL, 1M in ThF, 24.2 mmol) is slowly added by syringe and the reaction is monitored by TLC. Upon complete conversion, the reaction is carefully quenched using water, base, and water. Celite is added to the reaction, followed by diethyl ether and the mixture is then filtered through a celite plug. The two phases are then separated and the organic layer is washed using water and brine. The organic layer is the dried over anhydrous sodium sulfate and concentrated. The pure 2-[5-Propyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-ethanol (5.739 g, 18.2 mmol) is obtained in 75% yield after flash column chromatography.

Workup

  1. customUpon complete conversion, the reaction is carefully quenched
  2. additionCelite is added to the reaction
  3. filtrationthe mixture is then filtered through a celite plug
  4. customThe two phases are then separated
  5. washthe organic layer is washed
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-22f9c41e1e034d288932a1a704cd3fc7
Source dataset
uspto-grants-2009_05
Patent number
US07528160B2

Reaction notes

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