2-Mercaptoethanol → 2-[4-(4-Chloro-benzenesulfonyl)-5,8-difluoro-chroman-3-ylmethylsulfanyl]-ethanol

HRID 564328Notes

Reaction equation

HRID 564328 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]2[C:20]3[C:15](=[C:16]([F:22])[CH:17]=[CH:18][C:19]=3[F:21])[O:14][CH2:13][CH:12]2[CH2:23]OS(C)(=O)=O)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[SH:29][CH2:30][CH2:31][OH:32].[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([CH:11]2[C:20]3[C:15](=[C:16]([F:22])[CH:17]=[CH:18][C:19]=3[F:21])[O:14][CH2:13][CH:12]2[CH2:23][S:29][CH2:30][CH2:31][OH:32])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 15672-MercaptoethanolHCID 14798Sodium HydroxideHCID 72472590HCID 72472590, compound

Product 1

HCID 670063422-[4-(4-Chloro-benzenesulfonyl)-5,8-difluoro-chroman-3-ylmethylsulfanyl]-ethanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
77 °C

Procedure

Methanesulfonic acid 4-(4-chloro-benzenesulfonyl)-5,8-difluoro-chroman-3-ylmethyl ester described in Example 10, Step 6 (230 mg, 0.51 mmol) was dissolved in 7.0 mL of methanol and treated with 992 mg (12.7 mmol) of 2-mercaptoethanol and 2.0 mL of 1 M aqueous NaOH. The mixture was heated with a reflux condenser at 77° C. overnight. The mixture was cooled and partitioned between water and DCM. Aqueous phase was extracted with DCM. Combined organic phase was dried over MgSO4 and concentrated. The product was purified by column chromatography using 20% of EtOAc in hexanes as the eluent (140 mg, 63%)

Workup

  1. temperatureThe mixture was cooled
  2. custompartitioned between water and DCM
  3. extractionAqueous phase was extracted with DCM
  4. dry with materialCombined organic phase was dried over MgSO4
  5. concentrationconcentrated
  6. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-2c592f61f6e7477b887c743da4074bea
Source dataset
uspto-grants-2011_11
Patent number
US08067621B2

Reaction notes

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