3,3-Bis(hydroxymethyl)-2,3-dihydro-4H-1-benzothiopyran-4-one → HCID 59756936, compound

HRID 1009213Notes

Reaction equation

HRID 1009213 reaction equation
[OH:1][CH2:2][C:3]1([CH2:14][OH:15])[C:12](=[O:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[S:5][CH2:4]1.I([O-])(=O)(=O)=[O:17].[Na+]>CO.O>[OH:15][CH2:14][C:3]1([CH2:2][OH:1])[C:12](=[O:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[S:5](=[O:17])[CH2:4]1

Participants

5

Reactant 2

HCID 27640233,3-Bis(hydroxymethyl)-2,3-dihydro-4H-1-benzothiopyran-4-oneHCID 23667635Sodium periodate

Product 1

HCID 59756936HCID 59756936, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A solution of 3,3-bis(hydroxymethyl)thiochroman-4-one (200 mg, 0.9 mmol) in MeOH (5 ml) was admixed with a solution of sodium metaperiodate (206 mg, 0.96 mmol) in water (2 ml) and stirred at RT for 72 h. The reaction mixture was diluted with water (10 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, EtOAc), the desired product was obtained as a white solid (113 mg, 52% of theory, m.p. 108-111° C.).

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, EtOAc)

Sources & evidence

ORD record
ord-42f50f003db94066851b14c10cd962e1
Source dataset
uspto-grants-2011_07
Patent number
US07973072B2

Reaction notes

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