Diisobutylaluminum hydride → HCID 90418304, compound

HRID 2177140Notes

Reaction equation

HRID 2177140 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:13]([C:14](OCC)=[O:15])=[C:12]([C:19]([F:22])([F:21])[F:20])[S:11][N:10]=2)=[CH:5][CH:4]=1)[CH3:2].CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:13]([CH2:14][OH:15])=[C:12]([C:19]([F:22])([F:21])[F:20])[S:11][N:10]=2)=[CH:7][CH:8]=1)[CH3:2]

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 90418152HCID 90418152, compound

Product 1

HCID 90418304HCID 90418304, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-60 °C

Procedure

Into a 25-mL 3-necked round-bottom flask (1 atm) purged and maintained with an inert atmosphere of nitrogen, was placed ethyl 3-(4-ethylphenyl)-5-(trifluoromethyl)-1,2-thiazole-4-carboxylate (80 mg, 0.24 mmol, 1.00 equiv), toluene (2 mL). This was followed by the addition of DIBAL-H(25% in toluene) (0.690 g, 5.00 equiv) dropwise with stirring at −60° C. The resulting solution was stirred for 2 h at 28° C. The reaction progress was monitored by LCMS. The reaction mixture was cooled to 0° C. with a water/ice bath. The reaction was then quenched by the addition of 20 mL of water/NH4Cl. The resulting solution was extracted with 3×20 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 2×30 mL of sodium chloride. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by TLC-plate (EA: PE=4:1). This resulted in 0.056 g (80%) of [3-(4-ethylphenyl)-5-(trifluoromethyl)-1,2-thiazol-4-yl]methanol as a yellow solid. Mass spectrum (ESI, m/z): Calcd. for C13H12F3NOS, 288.1 (M+H). found 288.1.

Workup

  1. customInto a 25-mL 3-necked round-bottom flask (1 atm) purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. stirringThe resulting solution was stirred for 2 h at 28° C
  4. temperatureThe reaction mixture was cooled to 0° C. with a water/ice bath
  5. customThe reaction was then quenched by the addition of 20 mL of water/NH4Cl
  6. extractionThe resulting solution was extracted with 3×20 mL of ethyl acetate
  7. washThe resulting mixture was washed with 2×30 mL of sodium chloride
  8. dry with materialThe mixture was dried over anhydrous sodium sulfate
  9. concentrationconcentrated under vacuum
  10. customThe residue was purified by TLC-plate (EA: PE=4:1)
  11. customThis resulted in 0.056 g (80%) of [3-(4-ethylphenyl)-5-(trifluoromethyl)-1,2-thiazol-4-yl]methanol as a yellow solid

Sources & evidence

ORD record
ord-d14dee2488fb40fabdaacafa13449884
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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