Methanol → HCID 15546133, compound

HRID 399577Notes

Reaction equation

HRID 399577 reaction equation
[C:1]1(=[O:14])[N:5]([CH2:6][CH2:7][OH:8])[C:4](=[O:9])[C:3]2=[CH:10][CH:11]=[CH:12][CH:13]=[C:2]12.[H-].[Na+].[CH2:17](Br)[C:18]#[CH:19].CO>CN(C)C=O>[C:4]1(=[O:9])[N:5]([CH2:6][CH2:7][O:8][CH2:19][C:18]#[CH:17])[C:1](=[O:14])[C:2]2=[CH:13][CH:12]=[CH:11][CH:10]=[C:3]12

Participants

6

Reactant 4

HCID 887MethanolHCID 7842Propargyl bromideHCID 24758Sodium hydride3×HCID 77499N-(2-Hydroxyethyl)phthalimide

Product 1

HCID 15546133HCID 15546133, compoundYield 36.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of compound 3 (1.14 g, 5.96 mmol) in N,N-dimethylformamide (20 mL) was added NaH (0.36 g, 80%) dropwise. After complete NaH addition, stirring was continued for 0.5 h at room temperature, and then the reaction was cooled to 0° C. Propargyl bromide 4 (1.5 mL, 13.47 mmol) was added, and the stirring was continued for an additional 0.5 h at 0° C., then, at room temperature for 2 h. After careful addition of methanol to decompose excess NaH, the solvent was evaporated and the crude product was purified by flash column chromatography (3:2 to 1:1 to 2:3 hexane-ethyl acetate) to give compound 5 as a solid (495 mg, 36.2%) having an RF of 0.22 (3:2 hexane-ethyl acetate). See FIG. 5.

Workup

  1. waitthe stirring was continued for an additional 0.5 h at 0° C.
  2. waitat room temperature for 2 h
  3. customthe solvent was evaporated
  4. customthe crude product was purified by flash column chromatography (3:2 to 1:1 to 2:3 hexane-ethyl acetate)

Sources & evidence

ORD record
ord-4f5f8c05e0c34c8da178a83dc7479190
Source dataset
uspto-grants-1998_10
Patent number
US05821356

Reaction notes

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