Ammonium Chloride → HCID 18182494, compound

HRID 1359387Notes

Reaction equation

HRID 1359387 reaction equation
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=[CH:12][CH:11]=1.[NH+]1C=CC=CC=1.[F:22][C:23]([F:46])([F:45])[S:24]([O:27][C:28]1[C:29]([CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[N:30][C:31]([O:34][CH2:35][CH2:36][OH:37])=[CH:32][CH:33]=1)(=[O:26])=[O:25].C([Mg]Br)=C.[Cl-].[NH4+]>C(OCC)C.O1CCCC1.ClCCl>[F:46][C:23]([F:22])([F:45])[S:24]([O:27][C:28]1[C:29]([CH2:38][C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)=[N:30][C:31]([O:34][CH2:35][CH:36]([OH:37])[CH:11]=[CH2:12])=[CH:32][CH:33]=1)(=[O:25])=[O:26]

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 2724130Cornforth reagentHCID 18182223HCID 18182223, compoundHCID 178418507HCID 178418507, compound

Product 1

HCID 18182494HCID 18182494, compoundYield 11%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

473 mg of pyridinium dichromate was added to a mixture of 395 mg of 2-benzyl-6-(2-hydroxyethyl)oxy-3-pyridyl trifluoromethanesulfonate, 1.4 g of molecular sieves 4A and 5 ml of dichloromethane at room temperature, followed by stirring for 3 hours. The mixture was filtered through Celite, and the solvent was removed. 236 μl of a tetrahydrofuran solution containing 1.1 mol of vinylmagnesium bromide was added to a solution of 5 ml of diethyl ether containing the residue at 0° C., followed by stirring at the same temperature for 40 minutes. An aqueous saturated ammonium chloride solution and diethyl ether were added to the reaction solution, and the organic phase was washed with water and brine, dried over anhydrous magnesium sulfate and the solvent was removed. The residue was subjected to silica gel column chromatography using 30% ethyl acetate/hexane, to give 46.5 mg of the target compound.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customthe solvent was removed
  3. stirringby stirring at the same temperature for 40 minutes
  4. washthe organic phase was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed

Sources & evidence

ORD record
ord-880bf2f6dee84fdea50c488498419971
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

Loading…