Bis(2-chloroethyl) ether → HCID 23513805, compound

HRID 278317Notes

Reaction equation

HRID 278317 reaction equation
C(OC(=O)CS(C1C=CC(OCC#CC)=CC=1)(=O)=O)C.[CH2:21]([O:25][C:26]1[CH:31]=[CH:30][C:29]([S:32]([C:35]2([C:41]([O:43][CH2:44][CH3:45])=[O:42])[CH2:40][CH2:39][O:38][CH2:37][CH2:36]2)(=[O:34])=[O:33])=[CH:28][CH:27]=1)[C:22]#[C:23][CH3:24].C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1.ClCCOCCCl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(C(C)=O)C>[CH2:21]([O:25][C:26]1[CH:31]=[CH:30][C:29]([S:32]([C:35]2([C:41]([O:43][CH2:44][CH3:45])=[O:42])[CH2:40][CH2:39][O:38][CH2:37][CH2:36]2)(=[O:34])=[O:33])=[CH:28][CH:27]=1)[C:22]#[C:23][CH3:24]

Participants

7

Reactant 4

HCID 8115Bis(2-chloroethyl) etherHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 86757880HCID 86757880, compound

Product 1

HCID 23513805HCID 23513805, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6569Methyl Ethyl KetoneSolvent

Procedure

Ethyl 4-{[4-(2-butynyloxy)phenyl]sulfonyl}tetrahydro-2H-pyran-4-carboxylate (4-but-2-ynyloxy-benzenesulfonyl)-acetic acid ethyl ester (10 g, 33.8 mmol) was added to a stirring solution of potassium carbonate (12 g), 18-crown-6 (0.5 g), 2-chloroethyl ether (4.75 ml, 40.5 mmol), and tetrabutyl ammonium bromide (0.5 g) in methyl ethyl ketone (200 ml). The mixture was heated at reflux overnight before the salts were filtered off and the filtrate was concentrated. The residue was dissolved in chloroform and washed with water. The organic layer was dried over Na2SO4, filtered and concentrated. The compound was isolated using silica-gel column chromatography by eluting it with 20% ethyl acetate:hexane solution. Ethyl 4-{[4-(2-butynyloxy)phenyl]sulfonyl}tetrahydro-2H-pyran-4-carboxylate was isolated as a yellow oil (10.06 g). Yield 80%; MS: 367.2 (M+H)+

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight before the salts
  3. filtrationwere filtered off
  4. concentrationthe filtrate was concentrated
  5. dissolutionThe residue was dissolved in chloroform
  6. washwashed with water
  7. dry with materialThe organic layer was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe compound was isolated
  11. washby eluting it with 20% ethyl acetate

Sources & evidence

ORD record
ord-25c5eb51fb624e64b273c69167ba890e
Source dataset
uspto-grants-2002_03
Patent number
US06358980B1

Reaction notes

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