Cornforth reagent → HCID 53941841, compound

HRID 2256280Notes

Reaction equation

HRID 2256280 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH:5]([C:16]1[CH:24]=[CH:23][C:19]2[O:20][CH2:21][O:22][C:18]=2[CH:17]=1)[C:6]([N:8]([CH3:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:7].C1C=C[NH+]=CC=1.C1C=C[NH+]=CC=1.[O-][Cr](O[Cr]([O-])(=O)=O)(=O)=O>C(Cl)Cl>[O:1]=[CH:2][CH2:3][CH2:4][CH:5]([C:16]1[CH:24]=[CH:23][C:19]2[O:20][CH2:21][O:22][C:18]=2[CH:17]=1)[C:6]([N:8]([CH3:15])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:7]

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 54193565HCID 54193565, compound

Product 1

HCID 53941841HCID 53941841, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of β-(2-hydroxyethyl)-N-methyl-N-phenyl-1,3-benzodioxol-5-yl-propanamide (500 mg) in CH2Cl2 (10 mL) was treated with PDC (570 mg) and molecular sieves (4A, 570 mg) and stirred at room temperture for 2 hours. The reaction mixture was filtered through a pad of silica gel rinsed with EtOAc (100 mL) and concentrated under reduced pressure to yield an oil. Silica gel chromatography eluting with 50-75% EtOAc/Hexanes gave the desired title compound (374 mg).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of silica gel
  2. washrinsed with EtOAc (100 mL)
  3. concentrationconcentrated under reduced pressure
  4. customto yield an oil
  5. washSilica gel chromatography eluting with 50-75% EtOAc/Hexanes

Sources & evidence

ORD record
ord-326612def44b43838788b340a3da61b6
Source dataset
uspto-grants-1997_08
Patent number
US05654316

Reaction notes

Loading…