Triacetoxyperiodinane → HCID 178501146, compound

HRID 505270Notes

Reaction equation

HRID 505270 reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([O:11][CH3:12])=[O:10])[CH2:5][CH2:4]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl.CCOC(C)=O>[CH:2]([C@H:3]1[CH2:4][CH2:5][C@H:6]([C:9]([O:11][CH3:12])=[O:10])[CH2:7][CH2:8]1)=[O:1]

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 178501147HCID 178501147, compound

Product 1

HCID 178501146HCID 178501146, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a flask containing methyl trans-4-(hydroxymethyl)cyclohexanecarboxylate (100 mg, 0.581 mmol) in CH2Cl2 (5.8 mL) at 0° C., was added Dess-Martin periodinane (493 mg, 1.16 mmol). The reaction was allowed to warm to room temperature over an hour and then was diluted with EtOAc (60 mL), washed with saturated K2CO3 solution (3×40 mL) and brine (40 mL). The organic layer was dried over Na2SO4, filtered, and concentrated. Purification of the residue by flash chromatography on silica gel (0 to 25% EtOAc/hexanes) afforded methyl trans-4-formylcyclohexanecarboxylate. Rf=0.87 (25% EtOAc/hexanes). 1H NMR (CDCl3, 500 MHz) δ 9.63 (s, 1H), 3.67 (s, 3H), 2.51-2.05 (m, 6H), 1.63-1.26 (m, 4H).

Workup

  1. washwashed with saturated K2CO3 solution (3×40 mL) and brine (40 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification of the residue by flash chromatography on silica gel (0 to 25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-c9c564c38abd463894deb01d5fc025bf
Source dataset
uspto-grants-2010_08
Patent number
US07781426B2

Reaction notes

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