3-Furanol, tetrahydro- → 2-Phenyl-4-(3-tetrahydrofuranyl)-4H-1,3,4-oxadiazine-5(6H)-one

HRID 2416615Notes

Reaction equation

HRID 2416615 reaction equation
[C:1]1([C:7]2[O:8][CH2:9][C:10](=[O:13])[NH:11][N:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O[CH:15]1[CH2:19][CH2:18][O:17][CH2:16]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.C1(C)C=CC=CC=1>O1CCCC1>[C:1]1([C:7]2[O:8][CH2:9][C:10](=[O:13])[N:11]([CH:15]3[CH2:19][CH2:18][O:17][CH2:16]3)[N:12]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 99603-Furanol, tetrahydro-HCID 11776TriphenylphosphineHCID 142034742-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-5-oneHCID 66777355Diethylazodicarboxylate toluene

Product 1

HCID 121466812-Phenyl-4-(3-tetrahydrofuranyl)-4H-1,3,4-oxadiazine-5(6H)-oneYield 36%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-Phenyl-4H-1,3,4-oxadiazine-5(6H)-one (0.30 g) synthesized according to Receuil des Travaux chimiques des Pays Bas, 1929, 48, 417, 3-hydroxy tetrahydrofuran (0.30 g) and triphenyl phosphine (0.89 g) were dissolved in tetrahydrofuran (10 ml). Under ice-cooling, 40% diethyl azodicarboxylate/toluene solution (0.59 g) diluted with tetrahydrofuran (3 ml) was added thereto, followed by stirring overnight at room temperature. The reaction solution was evaporated and purified by Cromatorex NH silica gel chromatography (hexane/ethyl acetate system), to give the title compound (0.15 g, 36%).

Workup

  1. temperatureUnder ice-cooling
  2. additionwas added
  3. customThe reaction solution was evaporated
  4. custompurified by Cromatorex NH silica gel chromatography (hexane/ethyl acetate system)

Sources & evidence

ORD record
ord-90af1d464ae0411da8a4bb1a96b33d64
Source dataset
uspto-grants-2004_11
Patent number
US06825192B1

Reaction notes

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