Triacetoxyperiodinane → HCID 89872738, compound

HRID 515397Notes

Reaction equation

HRID 515397 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 89872740HCID 89872740, compound

Product 1

HCID 89872738HCID 89872738, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a round bottom flask containing 6-(4-bromophenyl)tetrahydro-2H-pyran-3-ol (638 mg, 2.48 mmol) was added DCM (16 ml). The mixture was stirred at room temperature before Dess-Martin Periodonane (1.3 g, 2.98 mmol) was added in several portions. After the addition, the reaction mixture was stirred for 2 hours before being quenched by a solution of saturated NaHCO3. The organic layer was washed with saturated NaHCO3 twice, then brine. The organic portion was dried over sodium sulfate, filtered and concentrated to afford a crude oil. Column purification afforded the title compound as a thick oil after drying (126 mg, 20% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.50-7.55 (m, 2H) 7.26-7.32 (m, 2H) 4.75 (dd, J=10.61, 2.78 Hz, 1H) 4.27-4.36 (m, 1H) 4.14-4.22 (m, 1H) 2.59-2.77 (m, 2H) 2.35 (ddt, J=13.74, 6.60, 3.35, 3.35 Hz, 1H) 2.11-2.24 (m, 1H).

Workup

  1. additionwas added in several portions
  2. additionAfter the addition
  3. custombefore being quenched by a solution of saturated NaHCO3
  4. washThe organic layer was washed with saturated NaHCO3 twice
  5. dry with materialThe organic portion was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford a crude oil
  9. customColumn purification

Sources & evidence

ORD record
ord-e74f3eaa30cb4dfd81fa52a5aa411b54
Source dataset
uspto-grants-2015_08
Patent number
US09108956B2

Reaction notes

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