Sodium Thiosulfate → HCID 89524836, compound

HRID 1620989Notes

Reaction equation

HRID 1620989 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2([CH2:12][OH:13])[CH2:11][O:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C([O-])(O)=O.[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2([CH:12]=[O:13])[CH2:9][O:10][CH2:11]2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 89524881HCID 89524881, compound

Product 1

HCID 89524836HCID 89524836, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The mixture of Example 86D (510 mg, 2.58 mmol) and Dess-Martin periodinane (1.3 g, 3.09 mmol) in 30 mL of dichloromethane was stirred under N2 atmosphere for 4 hours at room temperature. Then saturated NaHCO3 (120 mL) and Na2S2O3 (30 mL) was added with stirring for another 30 min. The mixture was extracted with dichloromethane (3×100 mL). The organic layers were combined, dried over Na2SO4, filtered, and concentrated to provide the crude product which was directly used in the next step without further purification.

Workup

  1. extractionThe mixture was extracted with dichloromethane (3×100 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f064751c70654408914aa12fe125ee52
Source dataset
uspto-grants-2014_07
Patent number
US08772500B2

Reaction notes

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