(2R)-2-(Phenoxymethyl)oxirane → (R)-2-Cyclohexyloxymethyl-oxirane
Reaction equation
[O:1]([CH2:8][C@H:9]1[CH2:11][O:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>O1CCCC1.[Ru]>[CH:2]1([O:1][CH2:8][C@H:9]2[CH2:11][O:10]2)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
In two separate runs, dissolve (R)-2-phenoxymethyl-oxirane (1.410 g, 9.389 mmol) in tetrahydrofuran (50 mL). Add 5% ruthenium on carbon (0.71 g) and hydrogenate at 60 psi of hydrogen gas for 40 minutes. Filter through a filtering agent, wash with tetrahydrofuran, concentrate and purify (silica gel chromatography, eluting with 5:95 to 30:70 ethyl acetate:hexanes) to give the desired compound as a clear liquid (0.850 g, 57.9% combined yield).
Workup
- customIn two separate runs
- filtrationFilter through a filtering agent
- washwash with tetrahydrofuran
- concentrationconcentrate
- custompurify
- wash(silica gel chromatography, eluting with 5:95 to 30:70 ethyl acetate:hexanes)
Sources & evidence
- ORD record
- ord-ac2d3327b15d47459b80b5ad7a66795f
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07745438B2
Reaction notes
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