Diisobutylaluminumhydride → 5-(1,1,1-Trifluoro-2-hydroxypropan-2-yl)pyridine-3-carbaldehyde

HRID 1048942Notes

Reaction equation

HRID 1048942 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]([C:6]1[CH:7]=[C:8]([C:12](OC)=[O:13])[CH:9]=[N:10][CH:11]=1)([OH:5])[CH3:4].[H-].C([Al+]CC(C)C)C(C)C>C1(C)C=CC=CC=1.ClCCl>[F:17][C:2]([F:1])([F:16])[C:3]([C:6]1[CH:7]=[C:8]([CH:12]=[O:13])[CH:9]=[N:10][CH:11]=1)([OH:5])[CH3:4]

Participants

5

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 68053841Methyl 5-(1,1,1-trifluoro-2-hydroxypropan-2-yl)pyridine-3-carboxylate

Product 1

HCID 867030845-(1,1,1-Trifluoro-2-hydroxypropan-2-yl)pyridine-3-carbaldehyde

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a cooled (−78° C.) solution of the title compound from Step B (0.14 g, 0.56 mmol) in toluene (3.23 mL) and dichloromethane (3.23 mL) was added a solution of di-isobutyl aluminum hydride in toluene (1.0 M, 1.29 mL, 1.29 mmol). After 10 min, the reaction was quenched with water (1 mL), allowed to warm to room temperature, and dried over magnesium sulfate. Concentration of the filtrate under reduced pressure provided the title compound: 1H NMR (500 MHz, CDCl3) δ 10.16 (s, 1 H), 9.08 (s, 1 H), 9.07 (s, 1 H), 8.41 (s, 1 H), 3.30 (br s, 1 H), 1.88 (s, 3 H).

Workup

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

Sources & evidence

ORD record
ord-7042f9eb45c249b4b074590ff1bd8ff0
Source dataset
uspto-grants-2016_07
Patent number
US09382226B2

Reaction notes

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