HCID 14497602, compound → HCID 53740142, compound

HRID 373490Notes

Reaction equation

HRID 373490 reaction equation
[CH3:1][Mg+].[Br-].[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:15]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[N:14]=[C:13]([CH2:24][CH2:25][C:26](=[O:28])[CH3:27])[CH:12]=2)=[CH:7][CH:6]=1>C1COCC1>[Cl:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[N:15]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[N:14]=[C:13]([CH2:24][CH2:25][C:26]([OH:28])([CH3:1])[CH3:27])[CH:12]=2)=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 14497602HCID 14497602, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 53740142HCID 53740142, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of MeMgBr (1.32 ml of 3.2M, 4.23 mM) in THF (15 ml) at 0° C., was added a solution of the ketone 23, (1.00 g, 2.82 mM) in THF (25 ml) dropwise over a 20 minute period. After stirring for 1 hour, the reaction mixture was quenched with a saturated NH4Cl solution, diluted to a 100 ml volume with Et2O, washed with H2O, dried (Na2SO4), filtered, and concentrated in vacuo. Chromatography of the residue (Baker silica gel, 45 g) with Et2O as eluent, afforded 27, (0.68 g, 80% corrected for recovered starting material) as a colorless oil.

Workup

  1. customthe reaction mixture was quenched with a saturated NH4Cl solution
  2. additiondiluted to a 100 ml volume with Et2O
  3. washwashed with H2O
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customChromatography of the residue (Baker silica gel, 45 g) with Et2O as eluent, afforded
  8. custom27, (0.68 g, 80% corrected for recovered starting material) as a colorless oil

Sources & evidence

ORD record
ord-6f7a1f13af5b4f2483a7aca359ac6814
Source dataset
uspto-grants-1992_11
Patent number
US05164381

Reaction notes

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