Pyridine → HCID 58923369, compound

HRID 1951045Notes

Reaction equation

HRID 1951045 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[OH:16][C:17]1[C:30]2[C:29](=[O:31])[C:28]3[C:23](=[C:24]([O:32][CH3:33])[CH:25]=[CH:26][CH:27]=3)[O:22][C:21]=2[CH:20]=[C:19](O)[CH:18]=1.N1C=CC=CC=1>C(Cl)Cl>[F:1][C:2]([F:15])([F:14])[S:3]([O:6][C:19]1[CH:18]=[C:17]([OH:16])[C:30]2[C:29](=[O:31])[C:28]3[C:23]([O:22][C:21]=2[CH:20]=1)=[C:24]([O:32][CH3:33])[CH:25]=[CH:26][CH:27]=3)(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 120264891,3-dihydroxy-5-methoxy-9H-xanthen-9-one

Product 1

HCID 58923369HCID 58923369, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoromethanesulfonic anhydride (3.1 mL, 18.43 mmol) was slowly added to a solution of 1,3-dihydroxy-5-methoxy-xanthen-9-one (3.32 g, 12.85 mmol) and pyridine (32.0 mL) in CH2Cl2 (130 mL) at 0° C. See, D. K. Ho et al., J. Org. Chem., 52, pp. 342-347 (1987). The reaction mixture then was allowed to slowly warm to RT and stirred for 16 h. The resulting orange mixture was concentrated to a brown oil, then dissolved in EtOAc (750 mL) and washed with 5% citric acid (3×100 mL), water (1×100 mL), and brine (1×100 mL). The organics were dried (MgSO4) and concentrated to yield 3.0 g (60%) of trifluoromethanesulfonic acid, 1-hydroxy-5-methoxy-9-oxo-9H-xanthen-3-yl ester as a light brown solid. Rf=0.65 (50% EtOAc/hexanes). 1H NMR (DMSO-d6, 400 MHz) δ: 12.89 (s, 1H), 7.74 (d, 1H), 7.60 (m, 1H), 7.50 (m, 1H), 7.42 (s, 1H), 7.04 (s, 1H), 3.97 (s, 3H).

Workup

  1. concentrationThe resulting orange mixture was concentrated to a brown oil
  2. dissolutiondissolved in EtOAc (750 mL)
  3. washwashed with 5% citric acid (3×100 mL), water (1×100 mL), and brine (1×100 mL)
  4. dry with materialThe organics were dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d4bc27013d0342d7980bd8552317b441
Source dataset
uspto-grants-2013_03
Patent number
US08404681B2

Reaction notes

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