Triacetoxyperiodinane → HCID 86761925, compound

HRID 448800Notes

Reaction equation

HRID 448800 reaction equation
[Br:1][C:2]1[C:3]([C:15]([P:18](=[O:25])([O:22][CH2:23][CH3:24])[O:19][CH2:20][CH3:21])([F:17])[F:16])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([CH:12]([OH:14])[CH3:13])[CH:6]=2.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>>[C:12]([C:7]1[CH:6]=[C:5]2[C:10]([CH:11]=[C:2]([Br:1])[C:3]([C:15]([P:18](=[O:25])([O:22][CH2:23][CH3:24])[O:19][CH2:20][CH3:21])([F:16])[F:17])=[CH:4]2)=[CH:9][CH:8]=1)(=[O:14])[CH3:13]

Participants

3

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 86761926HCID 86761926, compound

Product 1

HCID 86761925HCID 86761925, compound

Procedure

To a solution of diethyl [3-bromo-7-(1-hydroxyethyl)-2-naphthyl](difluoro)methylphosphonate (20 mg) from step 1, in CH12Cl2 (2 mL) at 0° C. was added Dess-Martin reagent (24 mg). The temperature was raised to rt and the reaction stirred for 1 h. The reaction was filtered on a pad of SiO2 eluting with 30% EtOAc/hexanes and the organics were evaporated to dryness. The residue was dissolved and hydrolysed with neat TMSBr (3 mL) and stirred at rt. overnight. The mixture was evaporated to dryness and the residue was dissolved in ethanol. It was evaporated to dryness again and the process was repeated 3 times. The reaction residue was dissolved in water, co-distilled with toluene and pumped with high vacuum to afford the titled product. 1H NMR (500 MHz, CD3OD): δ 8.79 (d, 1H), 8.50 (s, 1H), 8.39 (s, 1H), 8.15 (d, 1H), 8.02 (d 1H), 2.75 (s, 3H).

Workup

  1. filtrationThe reaction was filtered on a pad of SiO2 eluting with 30% EtOAc/hexanes
  2. customthe organics were evaporated to dryness
  3. dissolutionThe residue was dissolved and hydrolysed with neat TMSBr (3 mL)
  4. stirringstirred at rt
  5. customovernight
  6. customThe mixture was evaporated to dryness
  7. dissolutionthe residue was dissolved in ethanol
  8. customIt was evaporated to dryness again
  9. dissolutionThe reaction residue was dissolved in water, co-distilled with toluene

Sources & evidence

ORD record
ord-08b0e8da07be493cad69749ca66f4749
Source dataset
uspto-grants-2013_07
Patent number
US08481742B2

Reaction notes

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