Triacetoxyperiodinane → HCID 178471795, compound

HRID 505275Notes

Reaction equation

HRID 505275 reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[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[CH2:8][CH2:7][C@H:6]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:5][CH2:4]1)=[O:1]

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 178471796HCID 178471796, compound

Product 1

HCID 178471795HCID 178471795, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a 0° C. solution of ethyl [trans-4-(hydroxymethyl)cyclohexyl]acetate (102. 8 mg, 0.514 mmol) in CH2Cl2 (6 n-L) was added Dess-Martin periodinane. The reaction was warmed to room temperature and stirred for several hours. The reaction was then diluted with EtOAc (50 mL) and washed with 1N NaOH and brine (15 mL each). The organic layer was dried over Na2SO4, filtered, and concentrated. Purification of the residue by flash chromatography on silica gel (5 to 25% EtOAc/hexanes) afforded ethyl (trans-4-formylcyclohexyl)acetate. Rf=0.57 (40% EtOAc/hexanes). 1H NMR (CDCl3, 500 MHz) δ 9.61 (d, J=1.4 Hz, 1H), 4.13 (q, J=7.1 Hz, 2H), 2.13-2.22 (m, 3H), 1.98-2.01 (m, 2H), 1.87-1.91 (m, 2H), 1.77 (m, 1H), 1.31 (qd, J=13.0, 3.4 Hz, 2H), 1.25 (t, J=7.1 Hz, 3H), 1.05 (qd, J=13.0, 3.4 Hz, 2H).

Workup

  1. washwashed with 1N NaOH and brine (15 mL each)
  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 (5 to 25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-48e6be17ddd544d4a4dc441b2649b71e
Source dataset
uspto-grants-2010_08
Patent number
US07781426B2

Reaction notes

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