Toluene → HCID 86608602, compound

HRID 1786839Notes

Reaction equation

HRID 1786839 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[OH:12])[O:8][C:7](=[O:13])[CH2:6][CH:5]2[CH2:14]Cl.C1(C)C=CC=CC=1.N12CCCN=C1CCCCC2.[N:34]([CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][C:48]([OH:50])=[O:49])=[N+:35]=[N-:36]>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[OH:12])[O:8][C:7](=[O:13])[CH2:6][CH:5]2[CH2:14][O:50][C:48](=[O:49])[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][N:34]=[N+:35]=[N-:36]

Participants

6

Reactant 4

HCID 1140TolueneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 38110812-azidododecanoic acidHCID 68902517HCID 68902517, compound

Product 1

HCID 86608602HCID 86608602, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 6-bromo-4-chloromethyl-7-hydroxy-chroman-2-one (0.67 g, 2.3 mmol), dry toluene (3 mL), 1,8-diazabicyclo[5.4.0]undec-7-ene (1.4 g, 9.3 mmol) and 12-azido dodecanoic acid (0.84 g, 0.35 mmol) was refluxed for 2 h. The reaction mixture was allowed to cool to room temperature, diluted with chloroform (10 mL), quenched with 1N HCl, and the layers separated. The organic layer was dried over Na2SO4 and evaporated to yield the crude product Purification was done by column chromatography eluting with CH2Cl2 to afford the product (yield 60%). The characterization data were consistent with the proposed structure.

Workup

  1. temperaturewas refluxed for 2 h
  2. customquenched with 1N HCl
  3. customthe layers separated
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customevaporated
  6. customto yield
  7. customthe crude product Purification
  8. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-d7053640db7141f5b5a67d554a08a219
Source dataset
uspto-grants-2009_03
Patent number
US07507859B2

Reaction notes

Loading…