Diisobutylaluminum hydride → HCID 90418620, compound

HRID 2177227Notes

Reaction equation

HRID 2177227 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]([CH3:21])=[CH2:20])[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:8]=[CH:7][C:6]([C:9]2[C:13]([CH2:14][OH:15])=[C:12]([C:19]([CH3:21])=[CH2:20])[S:11][N:10]=2)=[CH:5][CH:4]=1)[CH3:2]

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 90417938HCID 90417938, compound

Product 1

HCID 90418620HCID 90418620, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-78 °C

Procedure

Into a 50-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of ethyl 3-(4-ethylphenyl)-5-(prop-1-en-2-yl)-1,2-thiazole-4-carboxylate (280 mg, 0.93 mmol, 1.00 equiv) in toluene (6 mL). DIBAL-H (1.32 g, 2.50 equiv) was added at −78° C. The resulting solution was stirred for 4 h at −78° C. The reaction was then quenched by the addition of 5 mL of water. The resulting solution was extracted with 200 mL of ethyl acetate. The organic layer was washed with 1×30 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The crude product was purified by TLC method with petroleum ether/ethyl acetate (3:1). This resulted in 305.3 mg (crude) of [3-(4-ethylphenyl)-5-(prop-1-en-2-yl)-1,2-thiazol-4-yl]methanol as yellow oil. Mass spectrum (ESI, m/z): Calcd. for C15H17NOS, 260.4 (M+H). found 260.4.

Workup

  1. customInto a 50-mL round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. customThe reaction was then quenched by the addition of 5 mL of water
  4. extractionThe resulting solution was extracted with 200 mL of ethyl acetate
  5. washThe organic layer was washed with 1×30 mL of brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under vacuum
  8. customThe crude product was purified by TLC method with petroleum ether/ethyl acetate (3:1)
  9. customThis resulted in 305.3 mg (crude) of [3-(4-ethylphenyl)-5-(prop-1-en-2-yl)-1,2-thiazol-4-yl]methanol as yellow oil

Sources & evidence

ORD record
ord-e403815345e34458b0a591b6d61e8ba2
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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