Diethyl Ether → HCID 11041211, compound

HRID 2408245Notes

Reaction equation

HRID 2408245 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[CH3:12]/[C:13](=[CH:18]\[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)/[CH2:14][CH2:15][CH2:16][OH:17].C(OCC)C>ClCCl>[CH3:12]/[C:13](=[CH:18]\[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)/[CH2:14][CH2:15][CH:16]=[O:17]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 12277043HCID 12277043, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 11041211HCID 11041211, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Solid pyridinium chlorochromate (4.21 g, 0.02 mol) was added in one portion to a cooled (−10° C.) solution of (4E)-4-methyl-5-phenyl-4-penten-1-ol (2.25 g, 0.013 mol) in dry dichloromethane (50 ml) under nitrogen. After 30 minutes, the reaction was warmed up to room temperature. After 1 hour, diethyl ether (250 ml) was added to the reaction. After stirring for 10 minutes, the reaction was filtered through silica gel and the solid rinsed with diethyl ether. The solvent was removed under vacuum and the residue was purified by column chromatography on silica gel (eluent: heptanes/ethyl acetate 25:1) followed by bulb-to-bulb distillation (82° C./0.002 mbar). 1.21 g (yield=53%) of the desired product was obtained.

Workup

  1. waitAfter 1 hour
  2. filtrationthe reaction was filtered through silica gel
  3. washthe solid rinsed with diethyl ether
  4. customThe solvent was removed under vacuum
  5. customthe residue was purified by column chromatography on silica gel (eluent: heptanes/ethyl acetate 25:1)
  6. distillationfollowed by bulb-to-bulb distillation (82° C./0.002 mbar)

Sources & evidence

ORD record
ord-50594e43e53e420bac32cfed260c2313
Source dataset
uspto-grants-2014_08
Patent number
US08815792B2

Reaction notes

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