Triacetoxyperiodinane → HCID 11051749, compound

HRID 1367673Notes

Reaction equation

HRID 1367673 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH3:23][C@@H:24]([CH2:27][CH2:28][CH2:29][C:30]([CH3:32])=[CH2:31])[CH2:25][OH:26]>C(Cl)Cl>[CH3:23][C@@H:24]([CH2:27][CH2:28][CH2:29][C:30]([CH3:32])=[CH2:31])[CH:25]=[O:26]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 18393302HCID 18393302, compound

Product 1

HCID 11051749HCID 11051749, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As reported by Schinzer et al.104 Dess-Martin periodinane (3.23 g, 7.61 mmol, 1.2 equiv) was added to a solution of alcohol 75 (0.9 g, 6.34 mmol) in methylene chloride (12 ml). The mixture was stirred at room temperature for 15 min before it was subjected to flash column chromatography (10% EtOAc/hexanes) to furnish aldehyde 67 (0.745 g, 84%) as highly volatile colorless liquid: [α]22D=+11.8 (c=0.5, CHCl3); TLC Rf=0.64 (silica gel, 25% EtOAc/hexanes); 1H NMR (600 MHz, CDCl3) δ 9.57-9.56 (d, 3J=1.8 Hz, 1H), 4.661 (s, 1H), 4.62 (s, 1H), 2.34-2.28 (m, 1H), 2.01-1.95 (t, 3J=7.8 Hz, 2H), 1.69-1.62 (m, 4H), 1.48-1.27 (m, 3H), 1.06-1.04 (d, 3J=6.6 Hz, 3H); 13C NMR (100 MHz, CDCl3) δ 205.282, 145.420, 110.441, 46.390, 37.845, 30.20, 24.969, 22.444, 13.523.

Sources & evidence

ORD record
ord-43e50cac0b5b4b8982950e149f9075ca
Source dataset
uspto-grants-2011_02
Patent number
US07893268B2

Reaction notes

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