HCID 14497520, compound → HCID 14497596, compound

HRID 373488Notes

Reaction equation

HRID 373488 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][CH:26]=[O:27])[CH:12]=2)=[CH:7][CH:6]=1>CCOCC>[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][CH:26]([OH:27])[CH3:1])[CH:12]=2)=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 14497520HCID 14497520, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 14497596HCID 14497596, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of methyl magnesium bromide (MeMgBr) (2.20 ml, 7.04 mM) in Et2O (15 ml) at 0° C. was added a solution of the aldehyde 11 (1.60 g, 4.69 mM)in Et2O (70 ml) dropwise over a 30 minute period. After stirring for 1 hour the reaction was quenched with a saturated, aqueous NH4Cl solution. The reaction mixture was partitioned between EtOAc and H2O. The EtOAc solution was dried (MgSO4), filtered, and concentrated in vacuo. Chromatography (65 g, Baker 40 gm silica gel) of the residue with Et2O as eluent afforded 20 (1.33 g, 79%) as a clear light yellow oil.

Workup

  1. customwas quenched with a saturated, aqueous NH4Cl solution
  2. customThe reaction mixture was partitioned between EtOAc and H2O
  3. dry with materialThe EtOAc solution was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4455a9c717254d299d340cf36d4c3116
Source dataset
uspto-grants-1992_11
Patent number
US05164381

Reaction notes

Loading…