Cornforth reagent → HCID 15382607, compound

HRID 1857873Notes

Reaction equation

HRID 1857873 reaction equation
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[C:22]([C:26]1[CH:27]=[C:28]([C:34]2[S:38][C:37]([CH2:39][OH:40])=[CH:36][CH:35]=2)[CH:29]=[CH:30][C:31]=1[O:32][CH3:33])([CH3:25])([CH3:24])[CH3:23]>ClCCl>[C:22]([C:26]1[CH:27]=[C:28]([C:34]2[S:38][C:37]([CH:39]=[O:40])=[CH:36][CH:35]=2)[CH:29]=[CH:30][C:31]=1[O:32][CH3:33])([CH3:25])([CH3:23])[CH3:24]

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 15382606HCID 15382606, compound

Product 1

HCID 15382607HCID 15382607, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

7.15 g (19 mmol) of pyridinium dichromate and 350 ml of dichloromethane are introduced into a round-bottomed flask. A solution of 3.9 g (14 mmol) of 5-(3-tert-butyl-4-methoxyphenyl)-2-thiophenemethanol in 50 ml of dichloromethane is added dropwise, at 0° C., and the mixture is stirred at room temperature for two hours. The reaction medium is filtered through silica and, after evaporation, 3.26 g (84%) of the expected aldehyde are recovered, in the form of a brown oil.

Workup

  1. filtrationThe reaction medium is filtered through silica
  2. customafter evaporation, 3.26 g (84%) of the expected aldehyde
  3. customare recovered, in the form of a brown oil

Sources & evidence

ORD record
ord-25d9ed2d42e34f9285a4902515fb9694
Source dataset
uspto-grants-2000_11
Patent number
US06147255

Reaction notes

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