Aluminium lithium hydride → HCID 69058787, compound

HRID 860625Notes

Reaction equation

HRID 860625 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]1[N:7]=[C:8]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)[O:9][C:10]=1[CH2:11][CH3:12])C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[CH2:11]([C:10]1[O:9][C:8]([C:13]2[CH:14]=[CH:15][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:17][CH:18]=2)=[N:7][C:6]=1[CH2:5][CH2:4][OH:3])[CH3:12]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 69053468HCID 69053468, compound

Product 1

HCID 69058787HCID 69058787, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

[5-Ethyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-yl]-acetic acid ethyl ester (4.0 g, 12.22 mmol) in anhydrous tetrahydrofuran (100 mL) is cooled to 0° C. and a 1M LiAlH4 (12.2 mL, 12.2 mmol) solution is added slowly. The reaction is monitored by TLC until complete consumption of the starting material. The reaction is then carefully quenched with 2.4 mL water, 2.4 mL 5N NaOH and 7 mL water. The light tan solid is filter through celite and dried to give crude 2-[5-Ethyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-yl]-ethanol (2.74 g, 9.60 mmol) or 79% yield.

Workup

  1. customThe reaction is monitored by TLC until complete consumption of the starting material
  2. customThe reaction is then carefully quenched with 2.4 mL water, 2.4 mL 5N NaOH and 7 mL water
  3. filtrationThe light tan solid is filter through celite
  4. customdried

Sources & evidence

ORD record
ord-75fbb99ace71464794bb2c798c812c29
Source dataset
uspto-grants-2006_12
Patent number
US07153878B2

Reaction notes

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