Cornforth reagent → HCID 14281472, compound

HRID 231649Notes

Reaction equation

HRID 231649 reaction equation
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[CH3:22][C:23]([Si:26]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[O:27][CH2:28][CH2:29][C:30]1([CH2:37][CH3:38])[CH:35]([OH:36])[CH:34]=[CH:33][CH2:32][CH2:31]1)([CH3:25])[CH3:24]>CN(C)C=O.[Cl-].[Na+].O>[CH3:22][C:23]([Si:26]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)([C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1)[O:27][CH2:28][CH2:29][C:30]1([CH2:37][CH3:38])[C:35](=[O:36])[CH:34]=[CH:33][CH2:32][CH2:31]1)([CH3:24])[CH3:25]

Participants

5

Reactant 2

HCID 2724130Cornforth reagentHCID 14281471HCID 14281471, compound

Product 1

HCID 14281472HCID 14281472, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Pyridinium dichromate (64.45 g, 171.33 mmol) was added to a solution of 6-[2-[[(1,1-dimethylethyl)diphenylsilyl]oxy]ethyl]-6-ethyl-2-cyclohexenol (56.01 g, 137.06 mmol) in 274 mL of dry N,N-dimethylformamide at 0° C. under nitrogen. After 1 hour, the reaction was poured into 2L of brine and extracted with 10×500 mL of ether. The ethereal solutions were concentrated in vacuo and flash chromatographed in two batches (95 mm column, 51/2 inches of silica gel, 8% ethyl acetate in petroleum ether eluent) to afford 48.94 g (88%) of product as a pale yellow oil.

Workup

  1. extractionextracted with 10×500 mL of ether
  2. concentrationThe ethereal solutions were concentrated in vacuo and flash
  3. customchromatographed in two batches (95 mm column, 51/2 inches of silica gel, 8% ethyl acetate in petroleum ether eluent)

Sources & evidence

ORD record
ord-4ebc17502cd141239c93259c30c2111d
Source dataset
uspto-grants-1989_07
Patent number
US04847389

Reaction notes

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