Lithium → HCID 21300958, compound

HRID 854515Notes

Reaction equation

HRID 854515 reaction equation
C[O:2][C:3]([C:5]1[S:9][C:8]([C:10]2[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([C:20]([F:23])([F:22])[F:21])[CH:11]=2)=[N:7][C:6]=1[CH3:24])=O.[Li]>O1CCCC1>[F:23][C:20]([F:21])([F:22])[C:12]1[CH:11]=[C:10]([C:8]2[S:9][C:5]([CH2:3][OH:2])=[C:6]([CH3:24])[N:7]=2)[CH:15]=[C:14]([C:16]([F:17])([F:19])[F:18])[CH:13]=1

Participants

4

Reactant 2

HCID 3028194LithiumHCID 86604584HCID 86604584, compound

Product 1

HCID 21300958HCID 21300958, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

2-(3,5-Bis-trifluoromethyl-phenyl)-4-methyl-thiazole-5-carboxylic acid methyl ester (0.545 g, 1.42 mmol), is dissolved in anhydrous tetrahydrofuran (6 mL) and cooled to 0° C. with stirring under nitrogen. Lithium aluminumhydride, 1.0M in THF, (1.40 mL, 1.40 mmol) is added and the reaction is monitored by TLC. After the starting material is completely consumed, the reaction is quenched with water, base, more water, and celite added, followed by dilution with ether. The mixture is filtered through a plug of celite and the two phases are separated. The organic layer is washed with water and brine, dried over sodium sulfate, then concentrated. The residue is further purified using flash column chromatography. The [2-(3,5-Bis-trifluoromethyl-phenyl)-4-methyl-thiazol-5-yl]-methanol (0.460 g, 1.35 mmol) is formed in 95% yield.

Workup

  1. customAfter the starting material is completely consumed
  2. customthe reaction is quenched with water, base, more water, and celite
  3. additionadded
  4. filtrationThe mixture is filtered through a plug of celite
  5. customthe two phases are separated
  6. washThe organic layer is washed with water and brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customThe residue is further purified

Sources & evidence

ORD record
ord-38990cb9ef63406b90fb47f75294cdfa
Source dataset
uspto-grants-2007_08
Patent number
US07259175B2

Reaction notes

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