Triacetoxyperiodinane → HCID 86670045, compound

HRID 69096Notes

Reaction equation

HRID 69096 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[S:11][C:12]([CH2:17][OH:18])=[C:13]([O:15][CH3:16])[CH:14]=2)[CH:5]=[CH:4][C:3]=1[CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl.O>[F:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[S:11][C:12]([CH:17]=[O:18])=[C:13]([O:15][CH3:16])[CH:14]=2)[CH:5]=[CH:4][C:3]=1[CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 67235617HCID 67235617, compound

Product 1

HCID 86670045HCID 86670045, compoundYield 50.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 3-[2-fluoro-4-[[5-(hydroxymethyl)-4-methoxy-2-thienyl]methoxy]phenyl]propanoate (1.6 g, 4.3 mmol) in anhydrous dichloromethane (10 mL), cooled to 0° C., is added Dess-Martin periodinane (2.76 g, 6.5 mmol). The reaction mixture is warmed to room temperature and stirred for 2 hours. The reaction mixture is diluted with water (15 mL), extracted with ethyl acetate, washed with water (15 mL), brine (15 mL), dried over sodium sulfate, filtered, and evaporated to dryness. The crude material is purified by silica gel chromatography eluting with hexane:ethyl acetate (8.8:1.2) to give the title compound (0.8 g, 50%). ESI/MS m/z 367.1 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water (15 mL), brine (15 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe crude material is purified by silica gel chromatography
  7. washeluting with hexane:ethyl acetate (8.8:1.2)

Sources & evidence

ORD record
ord-cda24caefbb84fc38f28377a360040b8
Source dataset
uspto-grants-2014_09
Patent number
US08822486B2

Reaction notes

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