Triacetoxyperiodinane → HCID 22022215, compound

HRID 729778Notes

Reaction equation

HRID 729778 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[C:12]([CH2:14][OH:15])=[CH:11][CH:10]=[CH:9]2.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O>ClCCl>[CH3:1][O:2][CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[C:12]([CH:14]=[O:15])=[CH:11][CH:10]=[CH:9]2

Participants

4

Reactant 2

HCID 159087Triacetoxyperiodinane2×HCID 15305969[8-(Methoxymethyl)naphthalen-1-yl]methanol

Product 1

HCID 22022215HCID 22022215, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(8-Methoxymethyl-naphthalen-1-yl)-methanol (Tetrahedron Lett. 1997; 38, 8161-8164) (0.36 g, 1.8 mmol) was dissolved in dichloromethane (10 mL). To the solution was then added 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one, also known as Dess-Martin periodinane (1.5 g, 3.6 mmol). The reaction mixture was stirred for 1 hr, then partitioned with an aqueous saturated solution of thiosulfate and dichloromethane. The organic layer was washed with an aqueous saturated solution of thiosulfate, an aqueous saturated solution of sodium bicarbonate, brine, dried with Na2SO4, filtered and the solvent evaporated in vacuo to yield crude 8-methoxymethyl-naphthalene-1-carbaldehyde which was used directly into the next step.

Workup

  1. custompartitioned with an aqueous saturated solution of thiosulfate and dichloromethane
  2. washThe organic layer was washed with an aqueous saturated solution of thiosulfate
  3. dry with materialan aqueous saturated solution of sodium bicarbonate, brine, dried with Na2SO4
  4. filtrationfiltered
  5. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-34dc55ce832b4ed1ad23554e26808214
Source dataset
uspto-grants-2009_09
Patent number
US07582649B2

Reaction notes

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