Aluminium lithium hydride → HCID 58765700, compound

HRID 860619Notes

Reaction equation

HRID 860619 reaction equation
C([O:3][C:4](=O)[CH:5]([C:7]1[N:8]=[C:9]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)[S:10][C:11]=1[CH2:12][CH3:13])[CH3:6])C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:12]([C:11]1[S:10][C:9]([C:14]2[CH:15]=[CH:16][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:18][CH:19]=2)=[N:8][C:7]=1[CH:5]([CH3:6])[CH2:4][OH:3])[CH3:13]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 69055843HCID 69055843, compound

Product 1

HCID 58765700HCID 58765700, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2-[5-Ethyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-propionic acid ethyl ester (1.05 g, 3.06 mmol) is dissolved into anhydrous tetrahydrofuran (THF) (10 mL) and then cooled to 0° C. with stirring. Lithium aluminum hydride (3.10 mL, 1M in THF, 3.10 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-Ethyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-propan-1-ol (0.930 g, 2.95 mmol) is obtained in 95% 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-a71d7305b3f347bb93c76b825263652f
Source dataset
uspto-grants-2006_12
Patent number
US07153878B2

Reaction notes

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