Triacetoxyperiodinane → HCID 59803810, compound

HRID 1261096Notes

Reaction equation

HRID 1261096 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([CH3:26])=[C:11]([CH:15]([C:17]2[C:25]3[C:20](=[N:21][CH:22]=[CH:23][CH:24]=3)[NH:19][CH:18]=2)[OH:16])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>O1CCCC1>[CH2:1]([O:8][C:9]1[C:10]([CH3:26])=[C:11]([C:15]([C:17]2[C:25]3[C:20](=[N:21][CH:22]=[CH:23][CH:24]=3)[NH:19][CH:18]=2)=[O:16])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 59803862HCID 59803862, compound

Product 1

HCID 59803810HCID 59803810, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (3-Benzyloxy-2-methyl-phenyl)-(1H-pyrrolo[2,3-b]pyridin-3-yl)-methanol (624, 0.12 g, 0.35 mmol) in tetrahydrofuran (15 mL) was added Dess-Martin periodinane (0.37 g, 0.89 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 50 minutes, then quenched with a saturated solution of sodium thiosulfate, extracted with ethyl acetate, washed with sodium bicarbonate, brine, and dried over magnesium sulfate. After removal of solvent, the residue was washed with a mixture of ethyl ether and hexanes (1:1) to provide the compound as a yellow solid (P-1848, 108 mg, 90%). MS (ESI) [M+H+]+=343.22.

Workup

  1. customquenched with a saturated solution of sodium thiosulfate
  2. extractionextracted with ethyl acetate
  3. washwashed with sodium bicarbonate, brine
  4. dry with materialdried over magnesium sulfate
  5. customAfter removal of solvent
  6. washthe residue was washed with a mixture of ethyl ether and hexanes (1:1)

Sources & evidence

ORD record
ord-5d4608aebbae40dfbb8198f8e4689936
Source dataset
uspto-grants-2013_06
Patent number
US08470818B2

Reaction notes

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