Diisobutylaluminum hydride → (4-Chloroquinolin-6-yl)methanol

HRID 2261084Notes

Reaction equation

HRID 2261084 reaction equation
CO[C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10]N=[C:8]2[Cl:15])=[O:4].[CH3:16]C(C[AlH]CC(C)C)C>C1COCC1>[Cl:15][C:8]1[C:7]2[C:12](=[CH:13][CH:14]=[C:5]([CH2:3][OH:4])[CH:6]=2)[N:11]=[CH:10][CH:16]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 18925080Methyl 4-chloroquinazoline-6-carboxylate

Product 1

HCID 57469641(4-Chloroquinolin-6-yl)methanolYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

To a solution of methyl-4-chloroquinazoline-6-carboxylate (3.5 g, 0015 mol) in dry THF (35 mL) at −25° C. was added DIBAL-H (4.4 g, 0.031 mol) and stirred at −25° C. to RT for 2 h. The reaction mixture was cooled to −10° C. and quenched with 10% aqueous NaHCO3 (9 mL). The reaction mixture was extracted with ethylacetate (100 mL), washed with water, brine and dried. The solvent was removed under vacuum to give 4-chloroquinoline-6-yl methanol (2 g, 66%).

Workup

  1. customquenched with 10% aqueous NaHCO3 (9 mL)
  2. extractionThe reaction mixture was extracted with ethylacetate (100 mL)
  3. washwashed with water, brine
  4. customdried
  5. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-d4d4fdbbdfd34863a9f143cfbff3d516
Source dataset
uspto-grants-2010_12
Patent number
US07846925B2

Reaction notes

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