Propiolic Acid → HCID 18549798, compound

HRID 649821Notes

Reaction equation

HRID 649821 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 mol) in 200 mL of methylene chloride was added propiolic acid (7.1 mL, 115.6 immol), dicyclohexylcarbodiimide (20.0 g, 110.3 mnmol) and 4-dimethylaminopyridine (1.93 g, 15.8 mmol). The resulting mixture was allowed to stir at ambient temperature for 18 h. 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. 1H 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-fde67f9548824cf1921ad590d1101265
Source dataset
uspto-grants-2001_08
Patent number
US06271237B1

Reaction notes

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