Methanol → HCID 22226407, compound

HRID 399580

Reaction equation

HRID 399580 reaction equation
[C:1]1(=[O:17])[N:5]([CH2:6][CH2:7][O:8][CH2:9][CH2:10][OH:11])[C:4](=[O:12])[C:3]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:2]12.[H-].[Na+].[CH2:20](Br)[C:21]#[CH:22].CO>CN(C)C=O>[C:4]1(=[O:12])[N:5]([CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:22][C:21]#[CH:20])[C:1](=[O:17])[C:2]2=[CH:16][CH:15]=[CH:14][CH:13]=[C:3]12

Participants

6

Reactant 4

HCID 887MethanolHCID 7842Propargyl bromideHCID 24758Sodium hydride3×HCID 27554062-(2-(2-Hydroxyethoxy)ethyl)-1H-isoindole-1,3(2H)-dione

Product 1

HCID 22226407HCID 22226407, compoundYield 36.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of compound 15 (1.39 g, 5.91 mmol) in N,N-dimethylformamide (25 mL) was added NaH (0.33 g, 80%) dropwise. After complete NaH addition, stirring was continued for 0.5 h at room temperature and then cooled to 0° C. Propargyl bromide 4 (1.24 mL, 11.13 mmol) was added, and stirring was continued for 0.5 h at 0° C., then for 2 h at room temperature. After careful addition of methanol to decompose excess NaH, the solvent was evaporated and crude product was purified by flash column chromatography (3:2 to 1:1 to 2:3 hexane-ethyl acetate) to give compound 16 as a solid (591 mg, 36.6%) having an RF of 0.41 (solvent 3:2 hexane-ethyl acetate). See FIG. 9.

Workup

  1. stirringstirring
  2. waitwas continued for 0.5 h at 0° C.
  3. waitfor 2 h at room temperature
  4. customthe solvent was evaporated
  5. customcrude product was purified by flash column chromatography (3:2 to 1:1 to 2:3 hexane-ethyl acetate)

Sources & evidence

ORD record
ord-5c693489ab12461ba35e53d734258f4a
Source dataset
uspto-grants-1998_10
Patent number
US05821356

Linked notes

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