Cornforth reagent → HCID 178455050, compound

HRID 2307139Notes

Reaction equation

HRID 2307139 reaction equation
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=[O:2].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[Si:22]([O:29][C:30]1[CH:35]=[C:34]([O:36][Si:37]([C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:39])[CH3:38])[CH:33]=[CH:32][C:31]=1[C@H:44]1[CH2:49][CH2:48][C@H:47]([CH2:50][OH:51])[CH2:46][CH2:45]1)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23]>CN(C)C=O>[Si:22]([O:29][C:30]1[CH:35]=[C:34]([O:36][Si:37]([C:40]([CH3:42])([CH3:43])[CH3:41])([CH3:39])[CH3:38])[CH:33]=[CH:32][C:31]=1[C@H:44]1[CH2:45][CH2:46][C@H:47]([C:50]([OH:2])=[O:51])[CH2:48][CH2:49]1)([C:25]([CH3:26])([CH3:27])[CH3:28])([CH3:24])[CH3:23]

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 178455049HCID 178455049, compound

Product 1

HCID 178455050HCID 178455050, compoundYield 44.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Pyridinium dichromate (146 mg) was added to a stirred solution of cis/trans-[4-(2,4-bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexyl]methanol (50 mg) in N,N-dimethylformamide (1 ml) at room temperature under argon. After 24 hr, the reaction mixture was partitioned between water (20 ml) and diethyl ether (30 ml). The layers were separated and the aqueous layer was extracted with diethyl ether (2×30 ml). The combined organic extracts were dried over magnesium sulfate and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, ethyl acetate/petrol, 1:9 v/v) to give the title compound as a cream solid (23 mg, 44%); m/z (ES+) 465 (M+H)+.

Workup

  1. customthe reaction mixture was partitioned between water (20 ml) and diethyl ether (30 ml)
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with diethyl ether (2×30 ml)
  4. dry with materialThe combined organic extracts were dried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by flash column chromatography (SiO2, ethyl acetate/petrol, 1:9 v/v)

Sources & evidence

ORD record
ord-5e0dfa8bd81443efb8017c0401836cff
Source dataset
uspto-grants-2004_12
Patent number
US06828460B2

Reaction notes

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