HCID 19348623, compound → HCID 19348493, compound

HRID 1418199Notes

Reaction equation

HRID 1418199 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][OH:17])=[C:12]([O:18][CH3:19])[CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[Si:1]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]=[O:17])=[C:12]([O:18][CH3:19])[CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 19348623HCID 19348623, compound

Product 1

HCID 19348493HCID 19348493, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

87.65 g (1.01 mol) of manganese dioxide were added to a solution of 29.30 g of (4-t-butyldimethylsilyloxymethyl-2-methoxyphenyl)methanol [prepared as described in step (i) above] in 150 ml of methylene chloride, and the resulting mixture was stirred at room temperature for 2 hours. At the end of this time, 41.2 g (0.474 mol) of manganese dioxide were added, with stirring, to the mixture. The reaction mixture was then stirred at 30° C. for 1.5 hours and heated under reflux for 1 hour with stirring, after which it was filtered. The filtrate was freed from the solvent by distillation under reduced pressure, to give 27.29 g (a quantitative yield) of the title compound as an oily substance.

Workup

  1. stirringwith stirring, to the mixture
  2. stirringThe reaction mixture was then stirred at 30° C. for 1.5 hours
  3. temperatureheated
  4. temperatureunder reflux for 1 hour
  5. stirringwith stirring
  6. filtrationafter which it was filtered
  7. distillationThe filtrate was freed from the solvent by distillation under reduced pressure

Sources & evidence

ORD record
ord-489754252d734df4aea929ffdab97471
Source dataset
uspto-grants-1999_03
Patent number
US05880147

Reaction notes

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