Ethylene Oxide → HCID 21464451, compound

HRID 1940879

Reaction equation

HRID 1940879 reaction equation
[C:1]1([NH:7][C:8](=[O:15])[C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.[CH2:21]1[O:23][CH2:22]1.O1CCOCC1>O1CCCC1>[OH:23][CH2:22][CH2:21][C:14]1[CH:13]=[N:12][CH:11]=[CH:10][C:9]=1[C:8]([NH:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:15]

Participants

6

Reactant 4

HCID 6354Ethylene OxideHCID 312751,4-DioxaneHCID 220840N-PhenylisonicotinamideHCID 178418339Butyllithium

Product 1

HCID 21464451HCID 21464451, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-phenylisonicotinamide (1.98 g, 10 mmol) in tetrahydrofuran (40 ml) at -78° C. was added a solution of n-butyllithium (1.6M in hexanes; 13.5 ml, 21.6 mmol) and the resulting red solution stirrred for 40 minutes before addition of a solution of ethylene oxide in dioxane (3.56M; 3.0 ml, 11 mmol). After allowing the mixture to warm to room temperature over 21/2 hours, the reaction was quenched by addition of methanol (8 ml). The solvent was evaporated and the residue partitioned between ethyl acetate (70 ml) and water (25 ml). The organic layer was washed with saturated brine (25 ml), dried (MgSO4) and evaporated. The residue was chromatographed on silica eluting with 10% methanol/dichloromethane to afford the title compound as a solid (1.05 g, 43%); δH (CDCl3) 3.07 (2H, t, J 5.6 Hz, ArCH2 CH2OH), 3.70 (1H, br s, OH), 4.10 (2H, t, J 5.6 Hz, ArCH2 CH2OH), 7.15-7.19 (1H, m, ArH), 7.35-7.39 (2H, m, ArH), 7.49 (1H, d, J 5.2 Hz, ArH), 7.69-7.71 (2H, m, ArH), 8.44-8.48 (2H, m, ArH), 9.77 (1H, s, NH).

Workup

  1. customthe reaction was quenched by addition of methanol (8 ml)
  2. customThe solvent was evaporated
  3. customthe residue partitioned between ethyl acetate (70 ml) and water (25 ml)
  4. washThe organic layer was washed with saturated brine (25 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue was chromatographed on silica eluting with 10% methanol/dichloromethane

Sources & evidence

ORD record
ord-0430b92b9d694fa9a72bd1392d6bf059
Source dataset
uspto-grants-1997_12
Patent number
US05700941

Linked notes

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