HCID 22345633, compound → HCID 22345612, compound

HRID 584296Notes

Reaction equation

HRID 584296 reaction equation
[Si:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([OH:18])[CH2:16][CH3:17])=[CH:11][C:10]=1[CH2:19][CH3:20])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>ClCCl.[O-2].[O-2].[Mn+4]>[Si:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:18])[CH2:16][CH3:17])=[CH:11][C:10]=1[CH2:19][CH3:20])([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 22345633HCID 22345633, compound

Product 1

HCID 22345612HCID 22345612, compoundYield 62.8%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

11.1 g (37 mmol) of 1-[4-(tert-butyldimethylsilanyloxy)-3-ethylphenyl]propan-1-ol are placed in 100 ml of dichloromethane in a round-bottomed flask, and 32.8 g (377 mmol) of manganese dioxide are added. The medium is stirred overnight at room temperature. It is then filtered through Celite and rinsed with dichloromethane. The filtrate is evaporated and the residue is purified by chromatography on a column of silica eluted with a mixture of heptane and ethyl acetate (90/10) to give 6.8 g (62%) of the expected product in the form of an orange-colored oil.

Workup

  1. filtrationIt is then filtered through Celite
  2. washrinsed with dichloromethane
  3. customThe filtrate is evaporated
  4. customthe residue is purified by chromatography on a column of silica
  5. washeluted with a mixture of heptane and ethyl acetate (90/10)

Sources & evidence

ORD record
ord-6b7ccce0e17b4e73877e73db6ebaf2ab
Source dataset
uspto-grants-2005_08
Patent number
US06924400B2

Reaction notes

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