Pyridine → HCID 13519332, compound

HRID 2290803Notes

Reaction equation

HRID 2290803 reaction equation
N1C=CC=CC=1.[CH2:7]([O:14][C:15]1[CH:16]=[C:17]([CH2:29][CH:30]([OH:40])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH:18]=[CH:19][C:20]=1[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C(Cl)Cl>[CH2:7]([O:14][C:15]1[CH:16]=[C:17]([CH2:29][C:30](=[O:40])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH:18]=[CH:19][C:20]=1[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 1049PyridineHCID 13519325HCID 13519325, compound

Product 1

HCID 13519332HCID 13519332, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 15 ml of methylene chloride and 1.2 ml of pyridine was gradually added 2 g of chromic anhydride under cooling to 0° C. to -5° C. and after stirring the mixture for 10 minutes at 0° to -3° C., a solution of 0.9 g of 3,4-dibenzyloxyphenyl-2-undecanol in 3 ml of methylene chloride was added to the mixture. After further stirring the mixture for 20 minutes at 0° to 10° C., the supernatent methylene chloride solution was concentrated under reduced pressure. The residue was applied to silica gel column chromatography and eluted with toluene to provide 0.8 g of 1-(3,4-dibenzyloxyphenyl)-2-undecanone.

Workup

  1. temperatureunder cooling to 0° C. to -5° C.
  2. stirringAfter further stirring the mixture for 20 minutes at 0° to 10° C.
  3. concentrationthe supernatent methylene chloride solution was concentrated under reduced pressure
  4. washeluted with toluene

Sources & evidence

ORD record
ord-9b9d3343a14e40488c313e04ce2393fa
Source dataset
uspto-grants-1986_10
Patent number
US04618627

Reaction notes

Loading…