Triacetoxyperiodinane → HCID 86705754, compound

HRID 1054551Notes

Reaction equation

HRID 1054551 reaction equation
[Cl:1][C:2]1[C:23]([Cl:24])=[CH:22][C:5]2[N:6]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[C:7]([CH2:9][CH2:10][CH2:11][CH2:12][OH:13])=[N:8][C:4]=2[CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Cl:1][C:2]1[C:23]([Cl:24])=[CH:22][C:5]2[N:6]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[C:7]([CH2:9][CH2:10][CH2:11][CH:12]=[O:13])=[N:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 67814888HCID 67814888, compound

Product 1

HCID 86705754HCID 86705754, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(5,6-Dichloro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,3-benzodiazol-2-yl)butan-1-ol (1.008 g, 2.59 mmol) was dissolved in DCM (35 ml) and Dess-Martin reagent (1.208 g, 2.85 mmol) was added at r.t. under N2. The reaction was left for 2 hrs. The reaction was quenched by the addition of 1M Na2S2O3 solution (10 ml), sat. NaHCO3 solution (40 ml) and DCM (80 ml). The organic layer was separated and the aqueous layer was extracted with DCM (3×80 ml). The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo to give the crude product. The product was purified by silica flash column chromatography using between 15% EtOAc:85% heptanes and 100% EtOAc as eluent to give the product as a pale yellow oil (0.595 g, 59%): MS (ESI+) for C17H24Cl2N2O2Si m/z 388.4 [M+H]+; LC purity 91% (ret. time, 1.74 min); 1H NMR (500 MHz, CDCl3) δ 9.82 (s, 1H), 7.79 (s, 1H), 7.53 (s, 1H), 5.44 (s, 2H), 3.43-3.67 (m, 2H), 2.97 (t, J=7.49 Hz, 2H), 2.69 (t, J=7.25 Hz, 2H), 2.23 (quin, J=7.13 Hz, 2H), 0.78-1.02 (m, 2H), −0.02 (s, 9H).

Workup

  1. customThe reaction was quenched by the addition of 1M Na2S2O3 solution (10 ml), sat. NaHCO3 solution (40 ml) and DCM (80 ml)
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with DCM (3×80 ml)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give the crude product
  8. customThe product was purified by silica flash column chromatography

Sources & evidence

ORD record
ord-d21da1badb6f407db3124ed32f245350
Source dataset
uspto-grants-2016_07
Patent number
US09394310B2

Reaction notes

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