Triacetoxyperiodinane → HCID 59803810, compound

HRID 1098456Notes

Reaction equation

HRID 1098456 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-3cf464c4ab204ac086c5a67615eac52f
Source dataset
uspto-grants-2012_03
Patent number
US08143271B2

Reaction notes

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