Diisobutylaluminumhydride → 5-(2-Hydroxypropan-2-yl)nicotinaldehyde

HRID 1048950Notes

Reaction equation

HRID 1048950 reaction equation
[OH:1][C:2]([C:5]1[CH:6]=[C:7]([C:11](OC)=[O:12])[CH:8]=[N:9][CH:10]=1)([CH3:4])[CH3:3].[H-].C([Al+]CC(C)C)C(C)C>C1(C)C=CC=CC=1.ClCCl>[OH:1][C:2]([C:5]1[CH:6]=[C:7]([CH:11]=[O:12])[CH:8]=[N:9][CH:10]=1)([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 66684512Methyl 5-(2-hydroxypropan-2-yl)pyridine-3-carboxylate

Product 1

HCID 867030855-(2-Hydroxypropan-2-yl)nicotinaldehyde

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a cooled (−78° C.) solution of the title compound from Step B (0.50 g, 2.6 mmol) in toluene (15 mL) and dichloromethane (15 mL) was added a solution of diisobutyl aluminum hydride in toluene (1.0 M, 6.0 mL, 6.0 mmol). After 10 min, the reaction was quenched with water (5 mL), allowed to warm to room temperature and dried with magnesium sulfate. Concentration of the filtrate under reduced pressure provided the title compound: 1H NMR (500 MHz, CDCl3) δ 10.10 (s, 1 H), 8.99 (d, J=2.3 Hz, 1 H), 8.93 (s, 1 H), 8.30 (s, 1 H), 2.22 (br s, 1 H), 1.67 (s, 6 H).

Workup

  1. customthe reaction was quenched with water (5 mL)
  2. dry with materialdried with magnesium sulfate

Sources & evidence

ORD record
ord-a9958c0105344d328c238fa50fa90615
Source dataset
uspto-grants-2016_07
Patent number
US09382226B2

Reaction notes

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