Pyridine → HCID 19010792, compound

HRID 1741832Notes

Reaction equation

HRID 1741832 reaction equation
N1C=CC=CC=1.[CH2:7]([C:11]1[CH:16]=[CH:15][C:14]([CH:17]([OH:21])[CH2:18][CH:19]=[CH2:20])=[CH:13][CH:12]=1)[CH:8]([CH3:10])[CH3:9]>ClCCl.[O-2].[Cr+6].[O-2].[O-2]>[CH2:7]([C:11]1[CH:12]=[CH:13][C:14]([C:17](=[O:21])[CH2:18][CH:19]=[CH2:20])=[CH:15][CH:16]=1)[CH:8]([CH3:10])[CH3:9]

Participants

5

Reactant 2

HCID 1049PyridineHCID 190107494-(2-Methylpropyl)-α-2-propen-1-ylbenzenemethanol

Product 1

HCID 19010792HCID 19010792, compoundYield 81.6%

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of pyridine (1.98 ml) in dichloromethane (15 ml) was added chromium(VI) oxide (1.23 g) at 0° C. After 30 minutes, 1-(4-isobutylphenyl)-3-buten-1-ol (525 mg) in dichloromethane (2 ml) was added and stirred for 20 minutes at ambient temperature. The reaction mixture was filtered through Florisil and washed with ether. The filtrate was concentrated in vacuo and chromatographed on silica gel (hexane:dichloromethane=1:1) to give 1-(4-isobutylphenyl)-3-buten-1-one (424 mg).

Workup

  1. filtrationThe reaction mixture was filtered through Florisil
  2. washwashed with ether
  3. concentrationThe filtrate was concentrated in vacuo
  4. customchromatographed on silica gel (hexane:dichloromethane=1:1)

Sources & evidence

ORD record
ord-d7daae02ffee47a89fb280c653ca915a
Source dataset
uspto-grants-1994_08
Patent number
US05334716

Reaction notes

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