Diethyl Ether → p-Nitrobenzyl 2-(4-Acetylthio-2-oxo-1-azetidinyl)-2-triphenylphosphoranylideneacetate

HRID 426460Notes

Reaction equation

HRID 426460 reaction equation
N1C(C)=CC=CC=1C.[C:9]([S:12][CH:13]1[N:16]([CH:17](Cl)[C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=2)=[O:19])[C:15](=[O:32])[CH2:14]1)(=[O:11])[CH3:10].[C:33]1([P:39]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.CCOCC>O1CCOCC1>[C:9]([S:12][CH:13]1[N:16]([C:17](=[P:39]([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=2)=[O:19])[C:15](=[O:32])[CH2:14]1)(=[O:11])[CH3:10]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 79372,6-LutidineHCID 11776TriphenylphosphineHCID 13132062p-Nitrobenzyl 2-(4-Acetylthio-2-oxo-1-azetidinyl)-2-chloroacetate

Product 1

HCID 13132063p-Nitrobenzyl 2-(4-Acetylthio-2-oxo-1-azetidinyl)-2-triphenylphosphoranylideneacetate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2,6-Lutidine (2.14 g., 20 mmole) was added to a solution of p-nitrobenzyl 2-(4-acetylthio-2-oxo-1-azetidinyl)-2-chloroacetate (5.9 g., 16 mmole) and triphenylphosphine (5.8 g., 22 mmole) in dioxane (80 ml.). The solution was kept at 55° for 18 hours and then concentrated on a rotary evaporator. The residue was partitioned between brine and ethyl acetate and the organic phase was washed with brine, dried and concentrated. The residue was purified by chromatography over silica gel (ethyl acetate:petroleum ether, 1:2 v/v) to give 4.64 g. (48%) of the title ether.

Workup

  1. concentrationconcentrated on a rotary evaporator
  2. customThe residue was partitioned between brine and ethyl acetate
  3. washthe organic phase was washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography over silica gel (ethyl acetate:petroleum ether, 1:2 v/v)
  7. customto give 4.64 g

Sources & evidence

ORD record
ord-a0d1ecbf5e18486ca0aed3b4132e6b7a
Source dataset
uspto-grants-1979_10
Patent number
US04169833

Reaction notes

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