Tetrahydrofuran → HCID 131729882, compound

HRID 884382Notes

Reaction equation

HRID 884382 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:10][CH2:9][CH:8]([CH2:11][CH2:12]O)[N:7]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[O:5])[CH3:2].[N+:21]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[Se:30]C#N)([O-:23])=[O:22].C1COCC1.C(P(CCCC)CCCC)CCC>CC(OC)(C)C.N1C=CC=CC=1>[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:10][CH2:9][CH:8]([CH2:11][CH2:12][Se:30][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[N+:21]([O-:23])=[O:22])[N:7]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 13831TributylphosphineHCID 1039312-Nitrophenyl selenocyanateHCID 90048554HCID 90048554, compound

Product 1

HCID 131729882HCID 131729882, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

497 mg of alcohol 170 (1.73 mmol) was dissolved and 432 mg of ortho-nitrophenyl selenocyanate (1.90 mmol, 1.1 eq.) suspended in a solvent mixture consisting of 10 ml of anhydrous THF and 3 ml of anhydrous pyridine. This was followed by careful dropwise addition of 0.56 ml of tri-n-butylphosphine (2.25 mmol, 1.3 eq.) at 0° C. to obtain a dark-red solution. After one hour, the batch was diluted with 30 ml of MTBE, filtered over a small amount of silica gel and concentrated. The brown residue was purified using column chromatography over silica gel (EE/CH 1:3), thereby obtaining 685 mg of selenyl ether 171 (1.45 mmol, 84%) as an intensely yellow-colored oil.

Workup

  1. customto obtain a dark-red solution
  2. filtrationfiltered over a small amount of silica gel
  3. concentrationconcentrated
  4. customThe brown residue was purified

Sources & evidence

ORD record
ord-5a0267677f9042329075806eda5386f4
Source dataset
uspto-grants-2012_08
Patent number
US08242105B2

Reaction notes

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