Triacetoxyperiodinane → HCID 86635909, compound

HRID 561783Notes

Reaction equation

HRID 561783 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][O:10][CH3:11])=[CH:4][C:3]=1[CH2:12][OH:13].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][O:10][CH3:11])=[CH:4][C:3]=1[CH:12]=[O:13]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 66761660HCID 66761660, compound

Product 1

HCID 86635909HCID 86635909, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [2-chloro-5-(2-methoxyethyl)phenyl]methanol from the previous step (I eq.) in CH2Cl2 (0.4 M) was added Dess-Martin periodinane (1.2 eq.) portionwise. The resulting suspension was stirred at RT for 2 h. The reaction was quenched with sat. aq. NaHCO3 and sat. aq. NaHSO3. The biphasic mixture was allowed to stir at RT for 20 min before it was extracted with CH2Cl2. The combined organic extracts were washed with brine, dried over MgSO4 and filtered. Concentration of the filtrate in vacuo afforded a colorless oil. Purification of the crude product thus obtained by way of flash chromatography (SiO2, Hex→9:1 (v/v) Hex:EtOAc) afforded the title compound as a colorless oil.

Workup

  1. customThe reaction was quenched with sat. aq. NaHCO3 and sat. aq. NaHSO3
  2. stirringto stir at RT for 20 min before it
  3. extractionwas extracted with CH2Cl2
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customConcentration of the filtrate in vacuo afforded a colorless oil
  8. customPurification of the crude product
  9. customthus obtained by way of flash chromatography (SiO2, Hex→9:1 (v/v) Hex:EtOAc)

Sources & evidence

ORD record
ord-0ad744cab55542d8843b2214dd4c64cf
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

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