Water → (R)-2,2-dimethyl-4-((3-nitrophenoxy)methyl)-1,3-dioxolane
Reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:18][C@@H:19]1[CH2:23][O:22][C:21]([CH3:25])([CH3:24])[O:20]1.O>CN(C=O)C.CCCCC>[CH3:24][C:21]1([CH3:25])[O:20][C@H:19]([CH2:18][O:10][C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[CH2:23][O:22]1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 160 °C
Procedure
A mixture of 3-nitrophenol 102 (2.00 g, 14.4 mmol), potassium carbonate (4.96 g, 35.9 mmol) and (S)-4-(chloromethyl)-2,2-dimethyl-1,3-dioxolane 103 (2.55 mL, 18.7 mmol) in DMF (20 mL) was heated in a microwave reactor at 160° C. for 4 h. The crude reaction mixture was poured into H2O and extracted with dichloromethane (3×15 mL). The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. The crude residue was purified by chromatography using ethyl acetate: pentane to obtain (R)-2,2-dimethyl-4-((3-nitrophenoxy)methyl)-1,3-dioxolane 104 (1.90 g, 52% yield) as an amber-colored oil.
Workup
- customThe crude reaction mixture
- extractionextracted with dichloromethane (3×15 mL)
- dry with materialThe combined organic layers were dried (Na2SO4)
- concentrationconcentrated under reduced pressure
- customThe crude residue was purified by chromatography
Sources & evidence
- ORD record
- ord-b8fe2cc778254508a22a2e03f536412c
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09326986B2
Reaction notes
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