Triacetoxyperiodinane → 3-[4-(4-Acetyl-3-hydroxy-2-propyl-phenoxymethyl)-benzoyl]-benzonitrile

HRID 1818492Notes

Reaction equation

HRID 1818492 reaction equation
[C:1]([C:4]1[CH:27]=[CH:26][C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH:16]([OH:25])[C:17]3[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=3)[C:20]#[N:21])=[CH:12][CH:11]=2)=[C:6]([CH2:28][CH2:29][CH3:30])[C:5]=1[OH:31])(=[O:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl.C(=O)(O)[O-].[Na+]>[C:1]([C:4]1[CH:27]=[CH:26][C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([C:17]3[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=3)[C:20]#[N:21])=[O:25])=[CH:12][CH:11]=2)=[C:6]([CH2:28][CH2:29][CH3:30])[C:5]=1[OH:31])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 666995493-{[4-(4-Acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenyl]-hydroxy-methyl}-benzonitrile

Product 1

HCID 666995563-[4-(4-Acetyl-3-hydroxy-2-propyl-phenoxymethyl)-benzoyl]-benzonitrileYield 96.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Stir a solution of 3-{[4-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenyl]-hydroxy-methyl}-benzonitrile (110 mg, 0.264 mmol) in dichloromethane (5 mL) at 0° C. Add Dess-Martin periodinane (1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(H)-one) (120 mg, 0.29 mmol) and stir the reaction for 1.5 hr at room temperature. Dilute the reaction mixture with aqueous saturated sodium bicarbonate (50 mL) and extract with ethyl acetate (3×50 mL). Dry the combined extracts over sodium sulfate, filter and concentrate. Purify the residue via silica gel chromatography, eluting with 7:3 hexanes:ethyl acetate to afford the title compound as a white solid (105 mg, 95%). Mass spectrum (M+H) 414.

Workup

  1. customthe reaction for 1.5 hr at room temperature
  2. extractionextract with ethyl acetate (3×50 mL)
  3. dry with materialDry the combined extracts over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify the residue via silica gel chromatography
  7. washeluting with 7:3 hexanes

Sources & evidence

ORD record
ord-73558031cfb44267bb4fc1cd06c0aca1
Source dataset
uspto-grants-2009_10
Patent number
US07598423B2

Reaction notes

Loading…