EDTA disodium salt → 2,3-Diphenyl-oxirane
Reaction equation
[C:1]1(/[CH:7]=[CH:8]/[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC([O-])=O)CC(O)=O)CN(CC([O-])=O)CC(O)=[O:20].[Na+].[Na+].C(=O)(O)[O-].[Na+].OOS([O-])=O.[K+]>CCOC(C)=O.CCCCCC.O.C(#N)C>[CH:4]1[CH:5]=[CH:6][C:1]([C@@H:7]2[O:20][C@H:8]2[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:2][CH:3]=1Participants
Procedure
To an acetonitrile solution (1.5 mL) of trans-stilbene (18 mg. 0.1 mmol) and ketone 4 (29.6 mg, 0.1 mmol) at room temperature was added an aqueous Na2EDTA solution (1 mL, 4×10-4M). To this homogenous solution was added in portions a mixture of sodium bicarbonate (1.55 mmol) and Oxone® (1 mmol). The reaction was finished in 7 min as shown by TLC. The reaction mixture was poured into water (20 mL), extracted with CH2Cl2 (3×20 mL) and dried with Na2SO4. After removal of the solvent under reduced pressure, the residue was purified by flash column chromatography; 20 g of silica gel (Merck, 230-400 mesh) in 100 mL of n-hexane with 2 mL of NEt3 was poured into a flash column of 20 mm diameter. The column was eluted with n-hexane (50 mL), followed by 5% EtOAc/n-hexane (150 mL) to give trans-stilbene epoxide (19.4 mg. 99% yield), and 40% EtOAc/n-hexane to give ketone 4 (27.6 mg. 93% yield of recovery).
Workup
- additionTo this homogenous solution was added in portions
- extractionextracted with CH2Cl2 (3×20 mL)
- dry with materialdried with Na2SO4
- customAfter removal of the solvent under reduced pressure
- customthe residue was purified by flash column chromatography
- addition20 g of silica gel (Merck, 230-400 mesh) in 100 mL of n-hexane with 2 mL of NEt3 was poured into a flash column of 20 mm diameter
- washThe column was eluted with n-hexane (50 mL)
Sources & evidence
- ORD record
- ord-06d77dbe298648a7b3d5245ac4e357fa
- Source dataset
- uspto-grants-1998_06
- Patent number
- US05763623
Reaction notes
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