Triacetoxyperiodinane → HCID 86594391, compound

HRID 2428058Notes

Reaction equation

HRID 2428058 reaction equation
[CH2:1]([O:3][C:4](=[O:30])[CH:5]=[CH:6][C@@H:7]([CH3:29])[C@@H:8]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[CH2:9][C@H:10]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:11][OH:12])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:30])[CH:5]=[CH:6][C@@H:7]([CH3:29])[C@@H:8]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[CH2:9][C@H:10]([O:13][Si:14]([C:17]([CH3:20])([CH3:18])[CH3:19])([CH3:16])[CH3:15])[CH:11]=[O:12])[CH3:2]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 86594392HCID 86594392, compound

Product 1

HCID 86594391HCID 86594391, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The alcohol 59 (3.86 g, 8.34 mmol) in CH2Cl2 (20 mL) was treated with Dess-Martin periodinane (5.3 g, 12.5 mmol). After 1 h, the mixture was quenched with saturated NaHCO3 (50 mL). The aqueous layer was extracted with ethyl ether (20 mL×2) and the combined extracts were dried over anhydrous MgSO4. Filtration and concentration followed by short flash column chromatography (hexane/EtOAc 4:1) to remove the residue from Dess-Martin reagent provided the aldehyde as a colorless oil: 1H NMR (300 MHz, CDCl3) (s, 1H), 7.02. dd, J=15.9, 6.6 Hz, 1H), 5.77 (dd, J=15.9, 1.4 Hz, 1H), 4.15 (dq, J=1.0, 7.2 Hz, 2H), 4.07 (ddd, J=6.4, 4.8, 1.4 Hz, 1H), 3.84 (ddd, J=8.6, 6.8, 4.4 Hz, 1H), 2.52 (m, 1H), 1.66 (m, 2H), 1.25 (t, J=7.1 Hz, 3H), 0.99 (d, J=6.9 Hz, 3H), 0.89 (s, 9H), 0.86 (s, 9H), 0.07 (s, 3H), 0.05 (s, 3H), 0.03 (s, 6H).

Workup

  1. customthe mixture was quenched with saturated NaHCO3 (50 mL)
  2. extractionThe aqueous layer was extracted with ethyl ether (20 mL×2)
  3. dry with materialthe combined extracts were dried over anhydrous MgSO4
  4. filtrationFiltration and concentration
  5. customto remove the residue from Dess-Martin reagent

Sources & evidence

ORD record
ord-c71e2045ba8542ddba88eb37dee6d66c
Source dataset
uspto-grants-2011_06
Patent number
US07968736B2

Reaction notes

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