Ethanol → HCID 67262644, compound

HRID 252797Notes

Reaction equation

HRID 252797 reaction equation
[I-:1].[Br:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N+:8]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[C:7]([CH3:20])[C:6]2([CH3:22])[CH3:21].S(=O)(=O)(O)O.[CH2:28](O)[CH3:29]>>[I-:1].[Br:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N+:8]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:28][CH3:29])=[O:18])=[C:7]([CH3:20])[C:6]2([CH3:22])[CH3:21]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 67262677HCID 67262677, compound

Product 1

HCID 67262644HCID 67262644, compoundYield 82%

Procedure

To a 250 mL flask were added 16 (2.0 g, 4.17 mmol), ethanol (60 mL) and conc. sulfuric acid (0.2 mL). The mixture was heated at reflux for 2 h and then was cooled to rt. The ethanol was removed in vacuo and the residue was partitioned between water (40 mL) and DCM (80 mL). The organic layer was washed with 1 M HCl (40 mL), water (40 mL) and then with a solution of sodium iodide. It was dried (MgSO4) and evaporated in vacuo to afford 17 as a brown solid (1.74 g, 82%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 h
  3. customThe ethanol was removed in vacuo
  4. customthe residue was partitioned between water (40 mL) and DCM (80 mL)
  5. washThe organic layer was washed with 1 M HCl (40 mL), water (40 mL)
  6. dry with materialIt was dried (MgSO4)
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-b33accd379fb43f6a1d3010d550de4fb
Source dataset
uspto-grants-2011_01
Patent number
US07868157B2

Reaction notes

Loading…