Pyridine → HCID 86209428, compound

HRID 2110961Notes

Reaction equation

HRID 2110961 reaction equation
[S:1]([O:8]S(C(F)(F)F)(=O)=O)([C:4]([F:7])([F:6])[F:5])(=[O:3])=[O:2].[OH:16][C:17]1[CH:24]=[C:23](O)[CH:22]=[CH:21][C:18]=1[CH:19]=[O:20].N1C=CC=CC=1>ClCCl>[CH:19]([C:18]1[CH:21]=[CH:22][C:23]([O:8][S:1]([C:4]([F:7])([F:6])[F:5])(=[O:3])=[O:2])=[CH:24][C:17]=1[OH:16])=[O:20]

Participants

5

Reactant 3

HCID 1049PyridineHCID 72132,4-DihydroxybenzaldehydeHCID 67749Trifluoromethanesulfonic anhydride

Product 1

HCID 86209428HCID 86209428, compoundYield 57.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of triflic anhydride (1.77 ml, 10.5 mmol) in dichloromethane 10 ml) was added to a mixture of 2,4-dihydroxybenzaldehyde (1.38 g, 10 mmol) and pyridine (0.85 ml, 10.5 mmol) in dichloromethane (30 ml) at −70 C. Dry ice bath was removed and the reaction mixture was stirred for 2 h at room temperature. The reaction mixture was diluted with dichloromethane, washed with water, brine and evaporated in vacuo. The crude product was purified by column chromatography (silica gel, EA:Hex, 1:6) to give 1.55 g of trifluoro-methanesulfonic acid 4-formyl-3-hydroxy-phenyl ester (57%).

Workup

  1. customDry ice bath was removed
  2. additionThe reaction mixture was diluted with dichloromethane
  3. washwashed with water, brine
  4. customevaporated in vacuo
  5. customThe crude product was purified by column chromatography (silica gel, EA:Hex, 1:6)

Sources & evidence

ORD record
ord-a421a79206e642759c95ee37f4deebcf
Source dataset
uspto-grants-2009_04
Patent number
US07517992B2

Reaction notes

Loading…