Triacetoxyperiodinane → HCID 90408321, compound

HRID 1855085Notes

Reaction equation

HRID 1855085 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([C:14]23[CH2:21][CH2:20][C:17]([CH2:22][CH2:23][CH2:24][CH2:25][OH:26])([CH2:18][CH2:19]2)[CH2:16][O:15]3)[CH:11]=[CH:12][CH:13]=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.C([O-])(O)=O.[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl>[O:1]([C:8]1[CH:9]=[C:10]([C:14]23[CH2:21][CH2:20][C:17]([CH2:22][CH2:23][CH2:24][CH:25]=[O:26])([CH2:18][CH2:19]2)[CH2:16][O:15]3)[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 22607107sodium thiosulfate NaHCO3HCID 90408750HCID 90408750, compound

Product 1

HCID 90408321HCID 90408321, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0° C. solution of 4-(1-(3-phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)butan-1-ol (150 mg, 0.426 mmol) in DCM (3 mL) was added Dess-Martin periodinane (217 mg, 0.511 mmol) over 5 min. The reaction mixture was slowly warmed up to rt and stirred for 2 h. An aq. solution of saturated NaHCO3-Na2S2O3 was added, and the mixture was stirred at rt for 5 min. The organic layer was washed with brine, dried (MgSO4), and concentrated in vacuo. The crude product was purified by flash chromatography (SiO2; gradient from 0 to 40% EtOAc:hexanes) to afford the title compound as a white solid (120 mg, 80% yield). 1H NMR (400 MHz, CDCl3) δ 9.77 (t, J=1.5 Hz, 1H), 7.35-7.27 (m, 2H), 7.24 (s, 1H), 7.16-7.03 (m, 3H), 7.01-6.94 (m, 2H), 6.84 (ddd, J=8.0, 2.4, 1.0 Hz, 1H), 3.80 (s, 2H), 2.42 (td, J=7.3, 1.5 Hz, 2H), 2.07-1.96 (m, 4H), 1.76-1.55 (m, 6H), 1.23-1.10 (m, 2H).

Workup

  1. stirringthe mixture was stirred at rt for 5 min
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by flash chromatography (SiO2; gradient from 0 to 40% EtOAc:hexanes)

Sources & evidence

ORD record
ord-0b5188b955be40fba831004b2f5eec16
Source dataset
uspto-grants-2015_02
Patent number
US08962660B2

Reaction notes

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