Water → 3-(6-Chloropyridin-3-yl)-2-methylpropan-1-ol

HRID 2244779Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2244779
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH:9]([CH3:13])[C:10](O)=[O:11])=[CH:4][CH:3]=1.B.O.[OH-].[Na+]>C1COCC1>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH:9]([CH3:13])[CH2:10][OH:11])=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 6331BoraneHCID 14798Sodium HydroxideHCID 540894253-(6-Chloropyridin-3-yl)-2-methylpropanoic acid

Produkt 1

HCID 592152003-(6-Chloropyridin-3-yl)-2-methylpropan-1-olAusbeute 69,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 3-(6-chloropyridin-3-yl)-2-methylpropanoic acid (6.5 g, 32.6 mmol) in THF (75 mL) cooled in an ice-water bath was added a solution of 1 M borane in THF (48 mL, 48 mmol) in a rapid dropwise fashion. The mixture was stirred at room temperature for 4 h. Water (25 mL) was added carefully followed by 2 N NaOH solution. The two phases were separated and the aqueous phase washed with ether (100 mL). The organic phases were combined, dried over anhydrous MgSO4, filtered, and concentrated to give 4.2 g of the product as a nearly colorless oil in 69% crude yield. [M+H]+=186, 188; IR: 3414 (OH)

Aufarbeitung

  1. customThe two phases were separated
  2. washthe aqueous phase washed with ether (100 mL)
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-88d752ac0caa4c069465e3dd96981e4a
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07678920B2

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