(2R,3R)-2,3-Dimethyl-hexan-1-ol → (2R,3R)-2,3-Dimethyl-hexanal

HRID 132620Notes

Reaction equation

HRID 132620 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[CH3:12][C@H:13]([C@H:16]([CH3:20])[CH2:17][CH2:18][CH3:19])[CH2:14][OH:15]>ClCCl>[CH3:12][C@H:13]([C@H:16]([CH3:20])[CH2:17][CH2:18][CH3:19])[CH:14]=[O:15]

Participants

4

Reactant 2

HCID 57444838(2R,3R)-2,3-Dimethyl-hexan-1-olHCID 178418287HCID 178418287, compound

Product 1

HCID 57444839(2R,3R)-2,3-Dimethyl-hexanalYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Pyridinium chlorochromate (27.35 g, 126.9 mmol) and neutral alumina (96 g, 3.5 g per gram of pyridinium chlorochromate) in dry dichloromethane (200 mL) was stirred under nitrogen for 0.25 hours. (2R,3R)-2,3-Dimethyl-hexan-1-ol (5.0 g, 38.46 mmol) in dichloromethane (60 mL) was added and the resulting dark slurry was stirred at room temperature for 3 hours. The slurry was filtered through a short pad of silica eluting with excess dichloromethane. Evaporation of the solvent afforded the titled compound (4.1 g, 84% yield) as an oil: 1H NMR (400 MHz, CDCl3) δ ppm 0.8 (m, 3H) 0.9 (d, J=6.6 Hz, 3H) 1.0 (d, J=6.6 Hz, 3H) 1.2 (m, 4H) 1.8 (m, 1H) 2.2 (m, 1H) 9.6 (s, 1H).

Workup

  1. filtrationThe slurry was filtered through a short pad of silica eluting with excess dichloromethane
  2. customEvaporation of the solvent

Sources & evidence

ORD record
ord-4754ab6bea85416ba389693c3f41616a
Source dataset
uspto-grants-2008_06
Patent number
US07388023B2

Reaction notes

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