Diethyl Ether → HCID 131725168, compound

HRID 498103Notes

Reaction equation

HRID 498103 reaction equation
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[Si:22]([O:29]C1CCCCC(O)CCCC1)(C(C)(C)C)([CH3:24])[CH3:23].[C:41]([CH:45]1[CH2:54][CH2:53][CH2:52][CH2:51][C:50]([O:56][SiH](C)C)(O)[CH2:49][CH2:48][CH2:47][CH2:46]1)([CH3:44])([CH3:43])[CH3:42].CCOCC>ClCCl>[C:41]([CH:45]1[CH2:46][CH2:47][CH2:48][CH2:49][C:50](=[O:56])[CH:51]([O:29][SiH:22]([CH3:24])[CH3:23])[CH2:52][CH2:53][CH2:54]1)([CH3:42])([CH3:43])[CH3:44]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 2724130Cornforth reagent2×HCID 11778782HCID 11778782, compoundHCID 131725169HCID 131725169, compound

Product 1

HCID 131725168HCID 131725168, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.5 g of pyridinium dichromate was dissolved in 30 ml of dichloromethane, to the solution was added 0.77 g of 6-tert-butyldimethylsilyloxy-1-cyclodecanol prepared in above-described (a). The mixture was stirred at room temperature for one and a half hours. Then, another 2.5 g of pyridinium dichromate was added to the reaction solution and the reaction solution was stirred at room temperature for further three hours. To the reaction solution was added 50 ml of ether, followed by purifying by column chromatography on Florisil, and the eluate with ether was collected, to afford 0.73 g of the titled compound (b) as colorless liquid.

Workup

  1. stirringthe reaction solution was stirred at room temperature for further three hours
  2. customby purifying by column chromatography on Florisil
  3. customthe eluate with ether was collected

Sources & evidence

ORD record
ord-ccbb8d0c7bca43639e36cce1c0539f6e
Source dataset
uspto-grants-2005_09
Patent number
US06949585B2

Reaction notes

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