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

HRID 1048942Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1048942
[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]

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittel2×HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-7042f9eb45c249b4b074590ff1bd8ff0
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09382226B2

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