Sulfuric acid magnesium salt (1:1) → HCID 14871093, compound

HRID 729173Notes

Reaction equation

HRID 729173 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[N:11]=[C:10]([C:21](OCC)=[O:22])[CH:9]=2)=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[O-]S([O-])(=O)=O.[Mg+2]>C1COCC1.CCOCC.O.[OH-].[Na+]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[N:11]=[C:10]([CH2:21][OH:22])[CH:9]=2)=[CH:6][CH:7]=1

Participants

8

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 14871092HCID 14871092, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 14871093HCID 14871093, compoundYield 93%

Reagents, catalysts & solvents 4

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

A solution of compound 1 (9.1 g, 25.5 mM) in THF (50 ml) was added over 45 min to a stirred suspension of LiAlH4 (0.726 g, 19.1 mM) in THF (50 ml) at 0° C. and stirring continued for 1 hr. The suspension was diluted with Et2O (100 ml) and H2O (0.73 ml), 15% aq. NaOH (0.73 ml) and H2O (2.1 ml) were added in sequence. The mixture was stirred for 16 hr, MgSO4 added and the suspension stirred an additional hour, filtered and the solids washed with Et2O. The combined organic layer was concentrated in vacuo, the residue dissolved inhot EtOAc and crystallized by the addition of hexane to give pure 3 (7.43 g, 93%) as a white solid, mp 95°-97° C., MS, m/e 314 (M+).

Workup

  1. additionwere added in sequence
  2. stirringThe mixture was stirred for 16 hr
  3. stirringthe suspension stirred an additional hour
  4. filtrationfiltered
  5. washthe solids washed with Et2O
  6. concentrationThe combined organic layer was concentrated in vacuo
  7. dissolutionthe residue dissolved inhot EtOAc
  8. customcrystallized by the addition of hexane

Sources & evidence

ORD record
ord-df62ac33722245968952f9236167b584
Source dataset
uspto-grants-1991_09
Patent number
US05051518

Reaction notes

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