Triacetoxyperiodinane → HCID 121396395, compound

HRID 60722Notes

Reaction equation

HRID 60722 reaction equation
[CH3:1][C:2]1([CH3:12])[O:6][C@@H:5]2[O:7][C@H:8]([CH2:10][OH:11])[CH2:9][C@@H:4]2[O:3]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C1COCC1>[CH3:1][C:2]1([CH3:12])[O:6][C@@H:5]2[O:7][C@H:8]([CH:10]=[O:11])[CH2:9][C@@H:4]2[O:3]1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 58444042HCID 58444042, compound2×

Product 1

HCID 121396395HCID 121396395, compoundYield 60.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of [(3aS,5S,6aS)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methanol (compound 25e, 2 g, 11.5 mmol) in THF (20 mL) was added Dess-Martine periodinane (7.2 g, 17.2 mmol). After being stirred room temperature for 2 hours, the resulting solution was filtered and the filtrate was concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 1:3 EtOAc in petroleum ether) to afford 1.2 g of (3aS,5S,6aS)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde (compound 25f). MS obsd. (ESI+) [(M+NH4)+]: 190.

Workup

  1. filtrationthe resulting solution was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by column chromatography on silica gel (eluting with 1:3 EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-61196aa062d14cc3b45dcc468db3c2ef
Source dataset
uspto-grants-2016_09
Patent number
US09441008B2

Reaction notes

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