18-Crown-6 → HCID 13374538, compound

HRID 373788Notes

Reaction equation

HRID 373788 reaction equation
CC(C)([O-])C.[K+].[Cl:7][C:8]1[CH:9]=[C:10]([CH:19]=[CH:20][CH:21]=1)[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1O.C1OCCOCCOCCOCCOCCOC1.[CH2:40]([O:42][C:43](=[O:53])[NH:44][CH2:45][CH:46]([O:48]S(C)(=O)=O)[CH3:47])[CH3:41]>CS(C)=O>[CH2:40]([O:42][C:43](=[O:53])[NH:44][CH2:45][CH:46]([O:48][C:15]1[CH:16]=[CH:17][C:12]([O:11][C:10]2[CH:19]=[CH:20][CH:21]=[C:8]([Cl:7])[CH:9]=2)=[CH:13][CH:14]=1)[CH3:47])[CH3:41]

Participants

6

Reactant 4

HCID 2855718-Crown-6HCID 19808418HCID 19808418, compoundHCID 20238779HCID 20238779, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 13374538HCID 13374538, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Procedure

A solution of 15 g of potassium tert.-butoxide in 45 ml of dimethyl sulfoxide is added, with stirring and with slight external cooling, to a solution of 25.2 g of 3-chlorophenoxyphenol in 40 ml of dimethyl sulfoxide; 1.5 g of 18-Crown-6 are added, a solution of 28.3 g of 2-methylsulfonyloxypropylcarbamic acid ethyl ester in 30 ml of dimethyl sulfoxide is added dropwise at 15° C. within a period of one hour, and then the mixture is stirred firstly at 20° C.-22° C. for 5 hours and then at +55° C. for 19 hours. After cooling, the reaction mixture is poured onto ice-water and extracted repeatedly with ether, the combined ether phases are washed with water, and the solvent is distilled off. The crude product is purified further by chromatography over silica gel (eluant: diethyl ether/hexane, 1:9), yielding 2-[4-(3-chlorophenoxy)phenoxy]-propylcarbamic acid ethyl ester in the form of a pale yellow, viscous oil, n20D : 1.5500.

Workup

  1. waitat +55° C. for 19 hours
  2. temperatureAfter cooling
  3. additionthe reaction mixture is poured onto ice-water
  4. extractionextracted repeatedly with ether
  5. washthe combined ether phases are washed with water
  6. distillationthe solvent is distilled off
  7. customThe crude product is purified further by chromatography over silica gel (eluant: diethyl ether/hexane, 1:9)

Sources & evidence

ORD record
ord-93b76ff1bfca49089d9ca9ac576db45d
Source dataset
uspto-grants-1992_11
Patent number
US05166153

Reaction notes

Loading…