2-Ethyl-2-((2-Hydroxymethylphenyl)thiomethyl)hexenal → 2-Ethyl-2-((2-formylphenyl)thiomethyl)hexenal

HRID 1837649Notes

Reaction equation

HRID 1837649 reaction equation
[CH2:1]([C:3]([CH2:10][S:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][OH:19])([CH:6]=[CH:7][CH2:8][CH3:9])[CH:4]=[O:5])[CH3:2].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[CH2:1]([C:3]([CH2:10][S:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH:18]=[O:19])([CH:6]=[CH:7][CH2:8][CH3:9])[CH:4]=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 544309312-Ethyl-2-((2-Hydroxymethylphenyl)thiomethyl)hexenalHCID 178418287HCID 178418287, compound

Product 1

HCID 537561052-Ethyl-2-((2-formylphenyl)thiomethyl)hexenalYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3.7 g of 16, 5.6 g (0.026 mole) of pyridinium chlorochromate, 2 g of Celite and 30 mL of methylene chloride was stirred for 18 h and filtered through a bed of silica gel. The silica gel was eluted with methylene chloride. The combined methylene chloride eluant was purified by HPLC (20% ETOAc-hexane) to give 2.4 g (66%) of an oil.

Workup

  1. filtrationfiltered through a bed of silica gel
  2. washThe silica gel was eluted with methylene chloride
  3. customThe combined methylene chloride eluant was purified by HPLC (20% ETOAc-hexane)

Sources & evidence

ORD record
ord-5294f14cd8b14a3d80eadc3ac2bd81b6
Source dataset
uspto-grants-2004_08
Patent number
US06784201B2

Reaction notes

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