Sodium periodate → HCID 67298468, compound

HRID 1009214Notes

Reaction equation

HRID 1009214 reaction equation
[OH:1][CH2:2][C:3]1([CH2:15][OH:16])[C:12](=[O:13])[C:11]2[C:6](=[CH:7][C:8]([CH3:14])=[CH:9][CH:10]=2)[S:5][CH2:4]1.I([O-])(=O)(=O)=[O:18].[Na+]>CO.O>[OH:1][CH2:2][C:3]1([CH2:15][OH:16])[C:12](=[O:13])[C:11]2[C:6](=[CH:7][C:8]([CH3:14])=[CH:9][CH:10]=2)[S:5](=[O:18])[CH2:4]1

Participants

5

Reactant 2

HCID 23667635Sodium periodateHCID 67298693HCID 67298693, compound

Product 1

HCID 67298468HCID 67298468, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A solution of 3,3-bis(hydroxymethyl)-7-methylthiochroman-4-one (300 mg, 1.26 mmol) in MeOH (6 ml) was admixed with a solution of sodium metaperiodate (286 mg, 1.34 mmol) in water (3 ml) and stirred at RT overnight. The reaction mixture was diluted with water (20 ml) and extracted with EtOAc (3×30 ml), the combined organic phases were dried over sodium sulfate and the solvent was removed under reduced pressure. After column chromatography purification of the residue (silica gel, 4:1 cyclohexane/EtOAc, 1% by vol. of acetic acid), the desired product was obtained as a white solid (186 mg, 58% of theory).

Workup

  1. extractionextracted with EtOAc (3×30 ml)
  2. dry with materialthe combined organic phases were dried over sodium sulfate
  3. customthe solvent was removed under reduced pressure
  4. customAfter column chromatography purification of the residue (silica gel, 4:1 cyclohexane/EtOAc, 1% by vol. of acetic acid)

Sources & evidence

ORD record
ord-2c841878d2474627998fbf403dfddc6d
Source dataset
uspto-grants-2011_07
Patent number
US07973072B2

Reaction notes

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