Diisobutylaluminum hydride → HCID 69722817, compound

HRID 1006030Notes

Reaction equation

HRID 1006030 reaction equation
[C:1]1([C:7]2[N:12]=[C:11]3[C:13](=[O:17])[CH2:14][O:15][CH2:16][C:10]3=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C[AlH]CC(C)C)C>ClCCl>[C:1]1([C:7]2[N:12]=[C:11]3[C:13]([OH:17])=[CH:14][O:15][CH2:16][C:10]3=[CH:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 22675556HCID 22675556, compound

Product 1

HCID 69722817HCID 69722817, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled solution (−70° C.) of 2-phenyl-8-oxopyrano[4,3-b]pyridine (1.09 g, 4.84 mmol) in dichloromethane (25 ml) was added DIBAL (IM in dichloromethane, 9 ml) keeping the temperature below −65° C. The reaction mixture was held at −70° C. for 4 hours. The reaction mixture was quenched by adding MeOH/dichloromethane (5 ml) (1/1), allowed to warm to ambient temperature and poured onto a slurry of SiO2 and dichloromethane. The silica slurry was applied to the top of a chromatography column which was eluted with methanol/dichloromethane to give 2-phenyl-8-hydroxypyrano-[4,3-b]pyridine as a pale yellow solid (0.89 g, 81%). (It was used immediately in the following step)

Workup

  1. customthe temperature below −65° C
  2. customThe reaction mixture was quenched
  3. additionby adding MeOH/dichloromethane (5 ml) (1/1)
  4. additionpoured onto a slurry of SiO2 and dichloromethane
  5. washwas eluted with methanol/dichloromethane

Sources & evidence

ORD record
ord-e3767c569c2b4e468b141bed2e9058a1
Source dataset
uspto-grants-2004_09
Patent number
US06787562B2

Reaction notes

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