HCID 13731468, compound → HCID 13731469, compound

HRID 2291027Notes

Reaction equation

HRID 2291027 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[CH2:12]([O:19][CH2:20][C:21]1([CH2:27][CH2:28][O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[O:25][CH:24]([OH:26])[CH2:23][CH2:22]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(Cl)Cl.CCOCC>[CH2:12]([O:19][CH2:20][C:21]1([CH2:27][CH2:28][O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[O:25][C:24](=[O:26])[CH2:23][CH2:22]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 13731468HCID 13731468, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 13731469HCID 13731469, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1.6 g (7.4 mmol) of pyridinium chlorochromate in 25 ml of methylene chloride under a nitrogen atmosphere, was added 13.5 g (6.5 mmol) of the compound prepared in (d) above in 25 ml of methylene chloride. After 18 hours at 25° C., the solution was diluted with 150 ml of ether, filtered through silica gel and the filtrate evaporated to afford an oil. The oil was then flash chromatographed on silica gel employing a mixture of petroleum ether and diethyl ether in a ratio of 7:3 as the eluent to yield colorless oil.

Workup

  1. filtrationfiltered through silica gel
  2. customthe filtrate evaporated
  3. customto afford an oil
  4. customflash chromatographed on silica gel employing
  5. additiona mixture of petroleum ether and diethyl ether in a ratio of 7:3 as the eluent
  6. customto yield colorless oil

Sources & evidence

ORD record
ord-09eaaa1f2dfa431ebcf2139a7972f4cf
Source dataset
uspto-grants-1986_10
Patent number
US04619917

Reaction notes

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