Diisobutylaluminum hydride → 4-(Quinolin-3-yl)-but-3-en-2-ol

HRID 1837921

Reaction equation

HRID 1837921 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([CH:11]=[CH:12][C:13](=[O:15])[CH3:14])[CH:2]=1.[AlH](CC(C)C)CC(C)C>C1COCC1>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([CH:11]=[CH:12][CH:13]([OH:15])[CH3:14])[CH:2]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 541844574-(Quinolin-3-yl)-but-3-en-2-one

Product 1

HCID 542299044-(Quinolin-3-yl)-but-3-en-2-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 22-1 (1.2 g, 6.1 mmol) in anhydrous THF (50 mL) was cooled to −78°, then treated dropwise with i-Bu2AlH (12.75 mL, 12.2 mmol). The resulting solution was stirred at −78° for 20 min, then quenched with ethyl acetate (20 mL), warmed to room temperature, treated with 1 M potassium sodium tartrate (25 mL) and stirred for 4 h. The mixture was extracted with ethyl acetate (2×150 mL) dried, filtered and evaporated to afford 22-2 as a yellow oil.

Workup

  1. customquenched with ethyl acetate (20 mL)
  2. additiontreated with 1 M potassium sodium tartrate (25 mL)
  3. stirringstirred for 4 h
  4. extractionThe mixture was extracted with ethyl acetate (2×150 mL)
  5. customdried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-f30aa161c8224ccab2189e84dc5191e2
Source dataset
uspto-grants-2004_08
Patent number
US06784190B2

Linked notes

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