Sodium periodate → HCID 86629116, compound

HRID 1013804Notes

Reaction equation

HRID 1013804 reaction equation
I([O-])(=O)(=O)=[O:2].[Na+].[Br:7][C:8]1[CH:23]=[CH:22][C:11]([CH2:12][CH:13]([CH2:19][CH:20]=C)[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:10]([Cl:24])[CH:9]=1>C1COCC1.O.O=[Os](=O)(=O)=O>[Br:7][C:8]1[CH:23]=[CH:22][C:11]([CH2:12][CH:13]([CH2:19][CH:20]=[O:2])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:10]([Cl:24])[CH:9]=1

Participants

6

Reactant 2

HCID 23667635Sodium periodateHCID 67316264Ethyl 2-(4-bromo-2-chlorobenzyl)pent-4-enoate

Product 1

HCID 86629116HCID 86629116, compoundYield 75.7%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Add sodium periodate (41 g, 190 mmol) into a solution of ethyl 2-(4-bromo-2-chlorobenzyl)pent-4-enoate (21 g, 63 mmol), 2.5 wt % OsO4 (64 g, 6.3 mmol) in THF (400 mL) and water (160 mL) and stir for 2 hours. Extract the reaction mixture with ethyl acetate, wash the organic layer with sodium thiosulfate solution and brine. Dry over sodium sulfate, filter and concentrate. Purify the residue with silica gel column to afford the title compound (15.9 g, 75%) as colorless oil: 1H NMR (CDCl3) 9.73 (s, 1H), 7.53 (d, J=2.0 Hz, 1H), 7.32 (dd, J=8.20, 2.0 Hz, 1H), 7.08 (d, J=8.2 Hz, 1H), 4.05-4.15 (m, 2H), 3.20-3.28 (m, 1H), 3.07-3.15 (m, 1H), 2.84-2.92 (m, 2H), 2.53-2.61 (m, 1H), 1.51-1.21 (m, 3H).

Workup

  1. extractionExtract the reaction mixture with ethyl acetate
  2. washwash the organic layer with sodium thiosulfate solution and brine
  3. dry with materialDry over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify the residue with silica gel column

Sources & evidence

ORD record
ord-0d43f0541051410c8b6fcf2aa5d5aa48
Source dataset
uspto-grants-2011_07
Patent number
US07981918B2

Reaction notes

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