HCID 54463571, compound → HCID 54363952, compound

HRID 2293776Notes

Reaction equation

HRID 2293776 reaction equation
[OH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][C:11]1[CH:25]=[CH:24][C:14]([CH:15]=[C:16]([N:21]=[N+]=[N-])[C:17]([O:19][CH3:20])=[O:18])=[CH:13][CH:12]=1>C1(C)C(C)=CC=CC=1>[OH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][C:11]1[CH:25]=[C:24]2[C:14]([CH:15]=[C:16]([C:17]([O:19][CH3:20])=[O:18])[NH:21]2)=[CH:13][CH:12]=1

Participants

3

Reactant 1

HCID 54463571HCID 54463571, compound

Product 1

HCID 54363952HCID 54363952, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Methyl 4-[(2-(2-hydroxyethoxy)ethoxy)ethoxy]-α-azidocinnamate (IV, EXAMPLE 2, 3.0 g) is dissolved in xylene (86 ml) and quickly heated to reflux. TLC indicates disappearance of starting material, the reaction is cooled to 20°-25° and the material is purified by flash column chromatography eluting with ethyl acetate/hexane (75/25). The appropriate fractions are pooled and concentrated to give the title compound, MS theory=323.1369, found=323.1366.

Workup

  1. temperaturequickly heated to reflux
  2. temperaturethe reaction is cooled to 20°-25°
  3. customthe material is purified by flash column chromatography
  4. washeluting with ethyl acetate/hexane (75/25)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a73dc769c1104fa7bb0fbbaf796ce06a
Source dataset
uspto-grants-1997_11
Patent number
US05686610

Reaction notes

Loading…