Pyridine → HCID 86209428, compound

HRID 751556Notes

Reaction equation

HRID 751556 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-73fa440d310846c4baa56f704d032abe
Source dataset
uspto-grants-2008_07
Patent number
US07405310B2

Reaction notes

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