Triacetoxyperiodinane → HCID 137328993, compound

HRID 1879498Notes

Reaction equation

HRID 1879498 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[C:23]([SiH2:27][O:28][C:29]([CH3:42])([CH3:41])[C:30]1[CH:31]=[C:32]([CH2:39][OH:40])[CH:33]=[C:34]([N:36]([CH3:38])[CH3:37])[CH:35]=1)([CH3:26])([CH3:25])[CH3:24].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:23]([SiH2:27][O:28][C:29]([CH3:42])([CH3:41])[C:30]1[CH:31]=[C:32]([CH:33]=[C:34]([N:36]([CH3:38])[CH3:37])[CH:35]=1)[CH:39]=[O:40])([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 137328992HCID 137328992, compound

Product 1

HCID 137328993HCID 137328993, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A suspension of Dess-Martin periodinane (available from Aldrich Chemical Company, Inc., 1001 West Saint Paul Avenue, Milwaukee, Wis. 53233, USA; 538 mg, 1.27 mmol) in methylene chloride (10 mL) was pipetted into a magnetically stirred solution of [3-(tert-butyl-dimethyl-silanyloxymethyl)-5-dimethylamino-phenyl]-methanol (288 mg, 0.986 mmol) in methylene chloride (20 mL). The mixture was stirred for 15 min. Powdered sodium bicarbonate (˜500 mg) was added and the volatiles were removed in vacuo. The residue was purified by silica gel chromatography, eluting with 10-40% ethyl acetate/hexanes, to give 3-(tert-butyl-dimethyl-silanyloxymethyl)-5-dimethylamino-benzaldehyde (187 mg, 65%) as a yellow oil.

Workup

  1. customthe volatiles were removed in vacuo
  2. customThe residue was purified by silica gel chromatography
  3. washeluting with 10-40% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-41a930700afd4ddcb82c2fc114e77f58
Source dataset
uspto-grants-2012_11
Patent number
US08314250B2

Reaction notes

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