Triacetoxyperiodinane → HCID 18617539, compound

HRID 1264231Notes

Reaction equation

HRID 1264231 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([C:12]([CH3:16])([CH3:15])[CH2:13][OH:14])=[CH:8][CH:7]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([C:12]([CH3:16])([CH3:15])[CH:13]=[O:14])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 18617744HCID 18617744, compound

Product 1

HCID 18617539HCID 18617539, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-furan-2-yl-phenyl)-2-methyl-propan-1-ol (6.56 g, 30 mmol) (reference example 53) in CH2Cl2 (200 mL) is added Dess-Martin periodinane (22.5 g, 53 mmol) and the resulting mixture stirred for 45 min then concentrated. The residue is purified by flash chromatography (eluting with 10% ethyl acetate in hexanes) to give 5.64 g of title compound. 1H NMR (CDCl3) δ 1.48 (s, 6H), 6.47 (m, 1H), 6.66 (d, J=3 Hz, 1H), 7.30 (d, J=8 Hz, 2H), 7.46 (s, 1H), 7.68 (d, J=8 Hz, 2H), 9.50 (s, 1H). MS (EI) m/z 214 (M+).

Workup

  1. concentrationthen concentrated
  2. customThe residue is purified by flash chromatography (eluting with 10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-6c67998bd24f4305b416481415e545e3
Source dataset
uspto-grants-2003_04
Patent number
US06541505B1

Reaction notes

Loading…