Pyridine → HCID 14621471, compound

HRID 1651669Notes

Reaction equation

HRID 1651669 reaction equation
N1C=CC=CC=1.[OH:7][CH2:8][C@H:9]1[C@@H:14]([CH2:15]/[CH:16]=[CH:17]\[CH2:18][CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])[CH2:13][O:12][C@@H:11]([CH3:25])[O:10]1>ClCCl.CCOCC.[O-2].[O-2].[O-2].[Cr+6]>[CH:8]([C@H:9]1[C@@H:14]([CH2:15]/[CH:16]=[CH:17]\[CH2:18][CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])[CH2:13][O:12][C@@H:11]([CH3:25])[O:10]1)=[O:7]

Participants

6

Reactant 2

HCID 1049PyridineHCID 14621469HCID 14621469, compound

Product 1

HCID 14621471HCID 14621471, compoundYield 67.7%

Reagents, catalysts & solvents 3

HCID 10219390chromium (VI) trioxideCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of pyridine (1.64 ml) in dichloromethane (45 ml) was added chromium trioxide (1.07 g) at 10° C. and the solution was stirred at room temperature for 1 hour. The solution was cooled in an ice bath and was added (2R,4R,5S)-4-hydroxymethyl-5-[(Z)-6-methoxycarbonyl-2-hexenyl]-2-methyl-1,3-dioxane (500 mg) in dichloromethane (3 ml). After being stirred at room temperature for 2 hours, the solution was diluted with ether (100 ml) and passed through a silica gel column. The eluate was evaporated in vacuo and the residue was chromatographed on a silica gel column (20 g) with a mixture of n-hexane and ethyl acetate (1:1) as an eluent to give (2R,4R,5S)-4-formyl-5-[(Z)-6-methoxycarbonyl-2-hexenyl]-2-methyl-1,3-dioxane (336 mg) as a colorless oil.

Workup

  1. temperatureThe solution was cooled in an ice bath
  2. stirringAfter being stirred at room temperature for 2 hours
  3. customThe eluate was evaporated in vacuo
  4. customthe residue was chromatographed on a silica gel column (20 g) with a mixture of n-hexane and ethyl acetate (1:1) as an eluent

Sources & evidence

ORD record
ord-afebc7f2e1324ab286e9cbb758434d87
Source dataset
uspto-grants-1990_05
Patent number
US04929639

Reaction notes

Loading…