Triacetoxyperiodinane → 4-Methyloxane-4-carbaldehyde

HRID 1962212Notes

Reaction equation

HRID 1962212 reaction equation
[CH3:1][C:2]1([CH2:8][OH:9])[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl.CCOCC>[CH3:1][C:2]1([CH:8]=[O:9])[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 59708470(4-Methyloxan-4-yl)methanol

Product 1

HCID 205923884-Methyloxane-4-carbaldehydeYield 68.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (4-methyl-tetrahydro-pyran-4-yl)-methanol (1.5 g, 11.5 mmol) in CH2Cl2 was added a suspension of Dess-Martin periodinane (5.8 g, 14 mmol) in CH2Cl2 (30 mL). After 70 min, the heterogenous mixture was diluted with Et2O (100 mL), stirred for 10 min, treated with 1 N HaOH (10 mL), and stirred for another 10 min. The mixture was filtered, and the filtrate was concentrated. The residue was purified by chromatography (Et2O/CH2Cl2) to give the title compound (1.01 g, 68%) as a colorless volatile oil. The spectral data matched that reported in PCT Intl. Pat. Appl. Publ. No. WO 2006/001752.

Workup

  1. additiontreated with 1 N HaOH (10 mL)
  2. stirringstirred for another 10 min
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by chromatography (Et2O/CH2Cl2)

Sources & evidence

ORD record
ord-7b153e4007f64650a54bba45492302ea
Source dataset
uspto-grants-2013_04
Patent number
US08415366B2

Reaction notes

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