Trifluoroacetic acid → 3-(2,3-dihydroxypropoxy)-1-hydroxy-5-methoxy-9H-xanthen-9-one

HRID 83096Notes

Reaction equation

HRID 83096 reaction equation
C(O)(C(F)(F)F)=[O:2].[OH:8][C:9]1[C:22]2[C:21](=[O:23])[C:20]3[C:15](=[C:16]([O:24][CH3:25])[CH:17]=[CH:18][CH:19]=3)[O:14][C:13]=2[CH:12]=[C:11]([O:26][CH2:27][CH:28]2[CH2:30][O:29]2)[CH:10]=1>>[OH:29][CH:28]([CH2:30][OH:2])[CH2:27][O:26][C:11]1[CH:10]=[C:9]([OH:8])[C:22]2[C:21](=[O:23])[C:20]3[C:15]([O:14][C:13]=2[CH:12]=1)=[C:16]([O:24][CH3:25])[CH:17]=[CH:18][CH:19]=3

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 444324121-hydroxy-5-methoxy-3-(oxiran-2-ylmethoxy)-9H-xanthen-9-one

Product 1

HCID 510381833-(2,3-dihydroxypropoxy)-1-hydroxy-5-methoxy-9H-xanthen-9-oneYield 47.3%

Conditions

Temperature
50 °C

Procedure

50% TFA (5 mL) was added to 1-hydroxy-5-methoxy-3-(oxiran-2-ylmethoxy)-9H-xanthen-9-one (20 mg, 0.06 mmol) synthesized in Step 2 of Example 1, and the reaction mixture was stirred at 50° C. for 4 hours. The solvent was removed, and the resulting residue was dried under reduced pressure to give the title compound (10 mg, 47.3%) as a white solid.

Workup

  1. customThe solvent was removed
  2. customthe resulting residue was dried under reduced pressure

Sources & evidence

ORD record
ord-60fbf569fa2e4366bbfbd4c7000bcbc2
Source dataset
uspto-grants-2014_09
Patent number
US08846749B2

Reaction notes

Loading…