HCID 23045067, compound → HCID 23045062, compound

HRID 2108039Notes

Reaction equation

HRID 2108039 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][OH:16].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl.CCOCC>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH:15]=[O:16]

Participants

5

Reactant 2

HCID 23045067HCID 23045067, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 23045062HCID 23045062, compoundYield 49.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 6-[2-(2-pyridinyl)ethoxy]hexanol (1.0 g) in dichloromethane (8 ml) was added dropwise over 15 min to a stirred suspension of pyridinium chlorochromate (1.83 g) and silica (Merck 7734, 2.9 g) in dichloromethane (30 ml). The mixture was stirred at room temperature under nitrogen for 4 h, diluted with ether (100 ml) and filtered through silica (Merck 9385, 200 ml), eluting with dichloromethane followed by methanol to give a brown oil. Purification by FCC eluting with ether gave the title compound as a yellow oil (0.49 g), t.l.c. (System A 40:10:1) Rf 0.42.

Workup

  1. filtrationfiltered through silica (Merck 9385, 200 ml)
  2. washeluting with dichloromethane
  3. customto give a brown oil
  4. customPurification by FCC
  5. washeluting with ether

Sources & evidence

ORD record
ord-e9b3c0a1d9f142b8943a4644fc7106f2
Source dataset
uspto-grants-1990_06
Patent number
US04937251

Reaction notes

Loading…