Triacetoxyperiodinane → HCID 23614737, compound

HRID 1768463Notes

Reaction equation

HRID 1768463 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH2:13][N:12]([C:14]([N:16]([CH3:18])[CH3:17])=[O:15])[C:11]([CH2:25][OH:26])([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:10]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH2:13][N:12]([C:14]([N:16]([CH3:18])[CH3:17])=[O:15])[C:11]([CH:25]=[O:26])([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:10]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 10247806HCID 10247806, compound

Product 1

HCID 23614737HCID 23614737, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 50 mg (0.14 mmol) of 1-9 in 1 mL of CH2Cl2 was added 71 mg (0.17 mmol) of Dess-Martin Periodinane (Lancaster Synthesis) and the mixture was left to stir for 15 min at room temperature. The reaction was diluted with 10 mL of CH2Cl2, quenched with 5 mL of 5% aqueous NaHSO3 and 10 mL of saturated aqueous NaHCO3 and the biphasic mixture was stirred for 30 min. The layers were separated, the organic was washed with NaHCO3 and water, dried over Na2SO4, and concentrated to provide 3-1 as a white solid. Data for 3-1: 1HNMR (500 MHz, CDCl3) δ 9.6 (s, 1H), 7.4-7.2 (m, 5H), 7.1-6.9 (m, 3H), 6.2 (s, 1H), 4.9 (d, 1H), 4.8 (d, 1H), 3.0 (s, 6H) ppm.

Workup

  1. waitthe mixture was left
  2. customquenched with 5 mL of 5% aqueous NaHSO3 and 10 mL of saturated aqueous NaHCO3
  3. stirringthe biphasic mixture was stirred for 30 min
  4. customThe layers were separated
  5. washthe organic was washed with NaHCO3 and water
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ae4afbec01a94d4ba3f7cda8c44feafa
Source dataset
uspto-grants-2007_06
Patent number
US07235580B2

Reaction notes

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