Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → Methyl 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)propyl]-oct-2-enoate

HRID 1494066Notes

Reaction equation

HRID 1494066 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([CH2:19][CH2:20][CH2:21][C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)[CH:17]=O)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C1(P(=[CH:47][C:48]([O:50][CH3:51])=[O:49])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([CH2:19][CH2:20][CH2:21][C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)[CH:17]=[CH:47][C:48]([O:50][CH3:51])=[O:49])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 102509236-(p-Chlorophenylsulfonamido)-2-[3-(3-pyridyl)propyl]-hexanal

Product 1

HCID 53687026Methyl 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)propyl]-oct-2-enoate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 3.08 g (7.5 mmol) of 6-(p-chlorophenylsulfonamido)-2-[3-(3-pyridyl)propyl]-hexanal in 40 mL chloroform is added 2.88 g (8.4 mmol) of methyl (triphenylphosphoranylidene)-acetate and then subjected to reflux for 3 hours. The solvent is evaporated and the residue taken up in ether and extracted with 0.5N HCl (3×20 mL). The aqueous extracts are combined and washed with ether. The aqueous phase is adjusted to pH 8 and then extracted with methylene chloride (3×50 mL). Combined organic extracts are dried (MgSO4), filtered and then evaporated to give an amber oil. This is purified by flash chromatography using 7:3 EtOAc: hexane as the eluent to give methyl 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)propyl]-oct-2-enoate as an oil.

Workup

  1. temperatureto reflux for 3 hours
  2. customThe solvent is evaporated
  3. extractionextracted with 0.5N HCl (3×20 mL)
  4. washwashed with ether
  5. extractionextracted with methylene chloride (3×50 mL)
  6. dry with materialCombined organic extracts are dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. customto give an amber oil
  10. customThis is purified by flash chromatography

Sources & evidence

ORD record
ord-7bcbdaa42f4640099660a82facca7c5f
Source dataset
uspto-grants-1991_06
Patent number
US05025025

Reaction notes

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