Hydrochloric Acid → 3-(3-chloro-2-mercaptopropoxy)-1-hydroxy-5-methoxy-9H-xanthen-9-one

HRID 83104Notes

Reaction equation

HRID 83104 reaction equation
[ClH:1].[OH:2][C:3]1[C:16]2[C:15](=[O:17])[C:14]3[C:9](=[C:10]([O:18][CH3:19])[CH:11]=[CH:12][CH:13]=3)[O:8][C:7]=2[CH:6]=[C:5]([O:20][CH2:21][CH:22]2[CH2:24][S:23]2)[CH:4]=1>C(OCC)(=O)C>[Cl:1][CH2:24][CH:22]([SH:23])[CH2:21][O:20][C:5]1[CH:4]=[C:3]([OH:2])[C:16]2[C:15](=[O:17])[C:14]3[C:9]([O:8][C:7]=2[CH:6]=1)=[C:10]([O:18][CH3:19])[CH:11]=[CH:12][CH:13]=3

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 510379581-hydroxy-5-methoxy-3-(thiiran-2-ylmethoxy)-9H-xanthen-9-one

Product 1

HCID 510381873-(3-chloro-2-mercaptopropoxy)-1-hydroxy-5-methoxy-9H-xanthen-9-oneYield 90.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Aqueous ethyl acetate 1M-HCl (3 mL) was added to 1-hydroxy-5-methoxy-3-(thiiran-2-ylmethoxy)-9H-xanthen-9-one (30 mg, 0.09 mmol) prepared in Example 3, followed by stirring at room temperature for 3 hours, and the reaction solvent was removed under reduced pressure. Ether was added to the residue, followed by sonication, and the solvent was removed to give the title compound (30 mg, 90.1%) as a light brown solid.

Workup

  1. customthe reaction solvent was removed under reduced pressure
  2. additionEther was added to the residue
  3. customfollowed by sonication
  4. customthe solvent was removed

Sources & evidence

ORD record
ord-40850f35bd4043ffb74512f0d25f7f83
Source dataset
uspto-grants-2014_09
Patent number
US08846749B2

Reaction notes

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