Propiolic Acid → HCID 18549798, compound

HRID 1266334Notes

Reaction equation

HRID 1266334 reaction equation
[N:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6][OH:7])=[N+:2]=[N-:3].[C:12](O)(=[O:15])[C:13]#[CH:14].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:12]([O:7][CH2:6][C:5]1[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=1[N:1]=[N+:2]=[N-:3])(=[O:15])[C:13]#[CH:14]

Participants

6

Reactant 3

HCID 10110Propiolic AcidHCID 10868DicyclohexylcarbodiimideHCID 124917242-Azidobenzenemethanol

Product 1

HCID 18549798HCID 18549798, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-azidobenzyl alcohol (15.66 g, 105.1 mmol) in 200 mL of methylene chloride was added propiolic acid (7.1 mL, 115.6 mmol), dicyclohexylcarbodiimide (20.0 g, 110.3 mmol) and 4-dimethylaminopyridine (1.93 g, 15.8 mmol). The resulting mixture was allowed to stir at ambient temperature for 18h. The mixture was filtered, concentrated and the residue was purified by flash chromatography (elution with 1:1 hexanes/ethyl acetate) to afford 10.7 g (51%) of the title compound. H NMR (CDCl3) δ7.40 (m, 2H), 7.17 (m, 2H), 5.20 (s, 2H), 2.92 (s, 1H).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. customthe residue was purified by flash chromatography (elution with 1:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-4cba8a9e41ff4e44932b24435cca2aa7
Source dataset
uspto-grants-2003_04
Patent number
US06548525B2

Reaction notes

Loading…