Triacetoxyperiodinane → HCID 86656260, compound

HRID 221386Notes

Reaction equation

HRID 221386 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([S:15]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][OH:26])[CH:20]=2)(=[O:17])=[O:16])=[CH:11][CH:10]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([S:15]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH:25]=[O:26])[CH:20]=2)(=[O:17])=[O:16])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 25097269HCID 25097269, compound

Product 1

HCID 86656260HCID 86656260, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2′,4′-dichloro-N-(3-(hydroxymethyl)phenyl)biphenyl-4-sulfonamide (340 mg, 0.83 mmol) in DCM (10 mL) was stirred under argon at room temperature. Dess-Martin reagent (390 mg, 0.92 mmol) was added in one portion and the mixture was stirred for an hour. The suspension was filtered through Celite, rinsing well with DCM. The filtrate was washed with 1 M Na2S2O3 (10 mL) and water (10 mL) and the DCM was dried over MgSO4. The solvent was evaporated and the residue absorbed onto SiO2 and purified by column chromatography (4×16 cm SiO2, 25% acetone/hexane) and the title compound obtained as a yellow waxy solid (280 mg).

Workup

  1. filtrationThe suspension was filtered through Celite
  2. washrinsing well with DCM
  3. washThe filtrate was washed with 1 M Na2S2O3 (10 mL) and water (10 mL)
  4. dry with materialthe DCM was dried over MgSO4
  5. customThe solvent was evaporated
  6. customthe residue absorbed onto SiO2
  7. custompurified by column chromatography (4×16 cm SiO2, 25% acetone/hexane)

Sources & evidence

ORD record
ord-8d61fe99e0a84cbe99e4463efd134ec5
Source dataset
uspto-grants-2012_06
Patent number
US08207167B2

Reaction notes

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