Triacetoxyperiodinane → HCID 86635918, compound

HRID 561811Notes

Reaction equation

HRID 561811 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][C:3]=1[CH2:11][OH:12].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][C:9]#[N:10])=[CH:4][C:3]=1[CH:11]=[O:12]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 66761775HCID 66761775, compound

Product 1

HCID 86635918HCID 86635918, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [4-chloro-3-(hydroxymethyl)phenyl]acetonitrile from the previous step (1 eq.) in CH2Cl2 (0.14 M) was added Dess-Martin periodinane (1.1 eq.) portionwise. The resulting suspension was stirred at RT for 3 h. The reaction was quenched with MeOH and H2O. The organic layer was separated and the aqueous layer was back-extracted with EtOAc. The combined organic extracts were washed sat. aq. NaHCO3 and brine, dried over Na2SO4 and filtered. Concentration of the filtrate in vacuo afforded the title compound as a pale yellow oil.

Workup

  1. customThe reaction was quenched with MeOH and H2O
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was back-extracted with EtOAc
  4. washThe combined organic extracts were washed sat. aq. NaHCO3 and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered

Sources & evidence

ORD record
ord-2ce5cc75865445d2bdc426c0c2cca71c
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

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