Propiolic Acid → Cgp-47292

HRID 218812Notes

Reaction equation

HRID 218812 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[C:3]=1[CH2:4][N:5]=[N+:6]=[N-:7].[C:13]([OH:17])(=[O:16])[C:14]#[CH:15].O=C1O[C@H]([C@H](CO)O)C(O)=C1O>[O-]S([O-])(=O)=O.[Cu+2].O.CC(O)(C)C>[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[C:3]=1[CH2:4][N:5]1[CH:15]=[C:14]([C:13]([OH:17])=[O:16])[N:7]=[N:6]1

Participants

6

Reactant 3

HCID 10110Propiolic AcidHCID 108883232-(Azidomethyl)-1,3-difluorobenzeneHCID 54670067L-Ascorbic Acid

Product 1

HCID 10014469Cgp-47292

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 714019492-Methylpropan-2-ol--water (1/1)Solvent

Procedure

2,6-Difluorobenzyl azide (III) (3.5 g, 20.7 mmoles) is suspended in a H2O-tBuOH 1:1 mixture (80 ml), then propiolic acid (1.59 g, 22.8 mmoles), an ascorbic acid 1M solution (2.1 ml) and a CuSO4 0.3 M solution (0.7 ml) are added thereto. The reaction mixture is kept at 40° C., under stirring and is completed after 2 h. The mixture is left to cool at room temperature thereby precipitating the product. The solid is filtered off on a Buchner filter, washed with ethyl ether and dried under vacuum.

Workup

  1. customis kept at 40° C.
  2. waitThe mixture is left
  3. customthereby precipitating the product
  4. filtrationThe solid is filtered off on a Buchner
  5. filtrationfilter
  6. washwashed with ethyl ether
  7. customdried under vacuum

Sources & evidence

ORD record
ord-c599605f36684ca597960f7f356f8a49
Source dataset
uspto-grants-2012_06
Patent number
US08198459B2

Reaction notes

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