Triacetoxyperiodinane → (S,4E)-3-(tert-Butyldimethylsilyloxy)-4-methyl-5-(2-methyl-thiazol-4-yl)-pent-4-enal

HRID 1740485Notes

Reaction equation

HRID 1740485 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[Si:23]([O:30][C@H:31](/[C:35](/[CH3:43])=[CH:36]/[C:37]1[N:38]=[C:39]([CH3:42])[S:40][CH:41]=1)[CH2:32][CH2:33][OH:34])([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]>C(Cl)Cl>[Si:23]([O:30][C@H:31](/[C:35](/[CH3:43])=[CH:36]/[C:37]1[N:38]=[C:39]([CH3:42])[S:40][CH:41]=1)[CH2:32][CH:33]=[O:34])([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:24])[CH3:25]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 10936330(-)-(3S,4E)-3-{[tert-Butyl(dimethyl)silyl]oxy}-4-methyl-5-(2-methyl-1,3-thiazol-4-yl)pent-4-en-1-ol

Product 1

HCID 11045612(S,4E)-3-(tert-Butyldimethylsilyloxy)-4-methyl-5-(2-methyl-thiazol-4-yl)-pent-4-enalYield 78.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A suspension of 478 mg (1.127 mmol, 1.3 equivalents) of Dess--Martin periodinane (1,1,1-triacetoxy-1,1-dihydro-1,2-benzodioxol-3(1H)-one) in 5.6 ml of absolute CH2Cl2 is mixed with a solution of 284 mg (0.87 mmol) of 14 in 5.0 ml of absolute CH2Cl2 and stirred for 60 minutes at room temperature. After the solvent is distilled off in a vacuum, the residue is flash-chromatographed by a silica gel column with pentane/Et2O (4:1). 222 mg (0.68 mmol, 78%) of 15 is obtained.

Workup

  1. distillationAfter the solvent is distilled off in a vacuum
  2. customthe residue is flash-chromatographed by a silica gel column with pentane/Et2O (4:1)

Sources & evidence

ORD record
ord-5d9d756a3fcb47d385c32f7f944eb798
Source dataset
uspto-grants-1999_10
Patent number
US05969145

Reaction notes

Loading…