Sodium sulfate decahydrate → HCID 57559932, compound

HRID 602683Notes

Reaction equation

HRID 602683 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)[N:9]2[CH2:12][C:11](=[C:13]([C:16]3[CH:21]=[C:20]([F:22])[CH:19]=[C:18]([F:23])[CH:17]=3)[CH:14]=[O:15])[CH2:10]2)=[CH:4][CH:3]=1.[CH3:31][Mg]Cl.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[Cl:30][C:27]1[CH:26]=[CH:25][C:24]([CH:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:9]2[CH2:12][C:11](=[C:13]([C:16]3[CH:17]=[C:18]([F:23])[CH:19]=[C:20]([F:22])[CH:21]=3)[CH:14]([OH:15])[CH3:31])[CH2:10]2)=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 86609769HCID 86609769, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 57559932HCID 57559932, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 805 mg (1.81 mmol) of {1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene}(3,5-difluorophenyl)acetaldehyde in 20 mL of THF was added slowly a solution of 1.33 mL (4.0 mmol) of methylmagnesium chloride (3.0M solution in TH) at −78° C. and stirred for 1 h. The reaction mixture was warmed to 0° C. for 1 h and 3 g of sodium sulfate decahydrate was added to quench the reaction, followed by stirring for 1 h at rt. The quenched reaction mixture was filtered and the organic layer was dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography with hexanes/acetone=8:1 to afford {1-[bis(4-chlorophenyl)methyl]azetidin-3-ylidene}-1-(3,5-difluorophenyl)propan-2-ol as a white solid. Mass Spectrum: m/e=460 (M+1 35Cl, 35Cl) and 462 (M+1 35Cl, 37Cl).

Workup

  1. customto quench
  2. customthe reaction
  3. stirringby stirring for 1 h at rt
  4. customThe quenched reaction mixture
  5. filtrationwas filtered
  6. dry with materialthe organic layer was dried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography with hexanes/acetone=8:1

Sources & evidence

ORD record
ord-2c60d90dcb044dd98fa081f3d2e8cc4c
Source dataset
uspto-grants-2011_03
Patent number
US07906503B2

Reaction notes

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