Dichloromethane → HCID 54097921, compound

HRID 1757271Notes

Reaction equation

HRID 1757271 reaction equation
C(Cl)Cl.[S:4]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]([CH:19]=[CH:20][CH:21]=2)[O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][OH:18])=[CH:5]1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.C([O-])(=O)C.[Na+]>C(OCC)C>[S:4]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]([CH:19]=[CH:20][CH:21]=2)[O:12][CH2:13][CH2:14][O:15][CH2:16][CH:17]=[O:18])=[CH:5]1

Participants

6

Reactant 4

HCID 6344Dichloromethane2×HCID 517045Sodium AcetateHCID 19390203HCID 19390203, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 54097921HCID 54097921, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A methylene chloride solution (2 ml) of 126 mg of 2-[2-[3-(3-thienyl)phenoxy]ethoxy]ethanol is added to a mixed solution of 352 mg of pyridinium chlorochromate, 274 mg of sodium acetate, 130 mg of molecular sieves (4A) and 5 ml of methylene chloride, the mixture is stirred at room temperature for 1.5 hours, the reaction solution is diluted with ethyl ether, silica gel is added, and the insoluble matters are removed by filtration. The filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography [Wako gel C-200, 10 g; hexane/ethyl acetate=4/1→2/1] to obtain 45 mg of the captioned compound as colorless oil.

Workup

  1. additionis added
  2. customthe insoluble matters are removed by filtration
  3. concentrationThe filtrate is concentrated under reduced pressure
  4. customthe residue is purified by silica gel column chromatography [Wako gel C-200, 10 g; hexane/ethyl acetate=4/1→2/1]

Sources & evidence

ORD record
ord-807d1475f6ec4fd6a10694af06f2b4a6
Source dataset
uspto-grants-1995_08
Patent number
US05444084

Reaction notes

Loading…