Propargyl alcohol → HCID 66738098, compound

HRID 558147Notes

Reaction equation

HRID 558147 reaction equation
[N:1]([CH2:4][CH2:5][N:6]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]1=[O:16])=[N+:2]=[N-:3].[CH2:17]([OH:20])[C:18]#[CH:19]>C1(C)C=CC=CC=1>[OH:20][CH2:17][C:18]1[N:1]([CH2:4][CH2:5][N:6]2[C:7](=[O:16])[C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:14]2=[O:15])[N:2]=[N:3][CH:19]=1

Participants

4

Reactant 2

HCID 7859Propargyl alcoholHCID 1902962-(2-Azidoethyl)-1H-isoindole-1,3(2H)-dione

Product 1

HCID 66738098HCID 66738098, compoundYield 31.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Heat a mixture of 2-(2-azidoethyl)isoindoline-1,3-dione (12 g, 55.5 mmol) and 2-propyn-1-ol (3.88 mL, 66.6 mmol) in toluene (50 mL) in a sealed reactor at 90° C. for 3 days. Cool to RT and collect the solid. Purify by column chromatography (DCM to 2% methanol in DCM) to give the title compound (first fraction) as a white solid (4.7 g, 31%). MS (ES) m/z 273 [M+1]+.

Workup

  1. temperatureHeat
  2. customcollect the solid
  3. customPurify by column chromatography (DCM to 2% methanol in DCM)

Sources & evidence

ORD record
ord-b5ac74f3a7f14d1ebbc0f60ada3dc6ba
Source dataset
uspto-grants-2011_11
Patent number
US08063035B2

Reaction notes

Loading…