Tetrahydrofuran → HCID 86760508, compound

HRID 1294354Notes

Reaction equation

HRID 1294354 reaction equation
C[C:2]([CH3:5])([O-:4])[CH3:3].[Na+].O1CCCC1.[I-].C[S+](C)C.OC(C1[C:24]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][CH2:38][C:39]3[N:40]=[C:41]([C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)[O:42][C:43]=3[CH3:44])=[CH:33][CH:32]=2)=[N:25][CH:26]=[CH:27][CH:28]=1)S([O-])(=O)=O.[Na+]>CS(C)=O.O>[CH3:44][C:43]1[O:42][C:41]([C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)=[N:40][C:39]=1[CH2:38][O:37][C:34]1[CH:33]=[CH:32][C:31]([CH2:30][O:29][C:24]2[C:3]([CH:2]3[CH2:5][O:4]3)=[CH:28][CH:27]=[CH:26][N:25]=2)=[CH:36][CH:35]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 75127Trimethylsulfonium iodideHCID 23676156Sodium t-butoxideHCID 86760509HCID 86760509, compound

Product 1

HCID 86760508HCID 86760508, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Procedure

Sodium t-butoxide (2.86 g) was added to dimethyl sulfoxide (20 ml), and after stirring at room temperature for 50 min., tetrahydrofuran (30 ml) was added and ice-cooled. Trimethylsulfonium iodide (4.04 g) was added to the mixture, and after stirring under ice-cooling for 10 min., a solution of sodium hydroxy[2-({4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyl}oxy)pyridin-3-yl]methanesulfonate (5 g) in dimethyl sulfoxide (15 ml) was dropwise added under ice-cooling and the mixture was stirred under ice-cooling for 1 hr. and at room temperature for 1 hr. The reaction solution was poured into iced water (100 ml) and extracted twice with t-butylmethyl ether (50 ml). The organic layers were combined, washed 4 times with water (50 ml) and concentrated under reduced pressure to give 2-({4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyl}oxy)-3-oxiran-2-ylpyridine.

Workup

  1. temperatureice-cooled
  2. stirringafter stirring under ice-
  3. temperaturecooling for 10 min.
  4. temperaturecooling
  5. stirringthe mixture was stirred under ice-
  6. temperaturecooling for 1 hr
  7. waitand at room temperature for 1 hr
  8. extractionextracted twice with t-butylmethyl ether (50 ml)
  9. washwashed 4 times with water (50 ml)
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cd6c084aa2964768bd1910a4508bf3fe
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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