Diisobutylaluminum hydride → HCID 90418631, compound

HRID 2177205Notes

Reaction equation

HRID 2177205 reaction equation
[F:1][C:2]([C:5]1[S:9][N:8]=[C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH3:17])=[CH:12][CH:11]=2)[C:6]=1[C:18](OCC)=[O:19])([F:4])[CH3:3].CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[F:1][C:2]([C:5]1[S:9][N:8]=[C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH3:17])=[CH:12][CH:11]=2)[C:6]=1[CH2:18][OH:19])([F:4])[CH3:3]

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 90418225HCID 90418225, compound

Product 1

HCID 90418631HCID 90418631, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-78 °C

Procedure

Into a 50-mL round-bottom flask (1 atm) purged and maintained with an inert atmosphere of nitrogen, was placed ethyl 5-(1,1-difluoroethyl)-3-(4-ethylphenyl)-1,2-thiazole-4-carboxylate (191 mg, 0.59 mmol, 1.00 equiv), toluene (3 mL). This was followed by the addition of DIBAL-H(25% in toluene) (1.67 g, 5.00 equiv) dropwise with stirring at −78° C. The resulting solution was stirred for 2 h at 30° C. The reaction progress was monitored by LCMS. The reaction mixture was cooled to 0° C. with a water/ice bath, then quenched by the addition of 10 mL of water and 10 mL NH4Cl. The resulting solution was extracted with 4×10 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 2×20 mL of sodium chloride. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by TLC-plate. This resulted in 32 mg (19%) of [5-(1,1-difluoroethyl)-3-(4-ethylphenyl)-1,2-thiazol-4-yl]methanol as a orange solid. Mass spectrum (ESI, m/z): Calcd. For C14H15F2NOS, 284.1 (M+H). found 284.1.

Workup

  1. customInto a 50-mL round-bottom flask (1 atm) purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. stirringThe resulting solution was stirred for 2 h at 30° C
  4. temperatureThe reaction mixture was cooled to 0° C. with a water/ice bath
  5. customquenched by the addition of 10 mL of water and 10 mL NH4Cl
  6. extractionThe resulting solution was extracted with 4×10 mL of ethyl acetate
  7. washThe resulting mixture was washed with 2×20 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
  11. customThis resulted in 32 mg (19%) of [5-(1,1-difluoroethyl)-3-(4-ethylphenyl)-1,2-thiazol-4-yl]methanol as a orange solid

Sources & evidence

ORD record
ord-901c74420a764a399c272e5037fa8063
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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