Diisobutylaluminum hydride → HCID 66760794, compound

HRID 561805Notes

Reaction equation

HRID 561805 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:15]=[C:14]([C:16](OCCC)=[O:17])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=1.CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:15]=[C:14]([CH2:16][OH:17])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 66761517HCID 66761517, compound

Product 1

HCID 66760794HCID 66760794, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of propyl 2-(3-methoxypropyl]quinoline-4-carboxylate from the previous step (1 eq.) in toluene (0.1 M) was added at −78° C. DIBAL (1.5 M toluene solution, 2 eq.) dropwise over 10 min. The reaction mixture was stirred at −78° C. for 30 min and then at 0° C. for 2 h. The reaction mixture was quenched with sat. aq. Rochelle's salt and extracted with EtOAc. The combined organic extracts were washed sequentially with water, sat. aq. NaHCO3 and brine. Drying over MgSO4, filtration and concentration of the filtrate in vacuo afforded the crude product as a milky oil. Purification by way of column chromatography (SiO2, 10:1 (v/v) Hex:EtOAc→EtOAc) afforded the title compound as a pale yellow oil.

Workup

  1. waitat 0° C. for 2 h
  2. customThe reaction mixture was quenched with sat. aq. Rochelle's salt
  3. extractionextracted with EtOAc
  4. washThe combined organic extracts were washed sequentially with water, sat. aq. NaHCO3 and brine
  5. dry with materialDrying over MgSO4, filtration and concentration of the filtrate in vacuo
  6. customafforded the crude product as a milky oil
  7. customPurification by way of column chromatography (SiO2, 10:1 (v/v) Hex:EtOAc→EtOAc)

Sources & evidence

ORD record
ord-1147230ab18142d395fbc3b02637adc4
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

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