Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → 4-Tert-butyl 1-methyl 2-(triphenylphosphoranylidene)succinate

HRID 1945051Notes

Reaction equation

HRID 1945051 reaction equation
[CH3:1][O:2][C:3](=[O:24])[CH:4]=[P:5]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Br[CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:24])[C:4](=[P:5]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28]

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 79177tert-Butyl bromoacetate

Product 1

HCID 110157884-Tert-butyl 1-methyl 2-(triphenylphosphoranylidene)succinate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (triphenylphosphanylidene)-acetic acid methyl ester (2.26 g, 6.77 mmol) in methylene chloride (25 mL) is added t-butyl bromoacetate (1.32 g, 6.77 mmol) and the mixture is stirred at room temperature for 48 hours. The solvent is removed under reduced pressure and the residue is purified by column chromatography using a gradient of 80-100% heptane/EtOAc to afford 2-(triphenylphosphanylidene)-succinic acid 4-tert-butyl ester 1-methyl ester. MS 449.3 (M+1).

Workup

  1. customThe solvent is removed under reduced pressure
  2. customthe residue is purified by column chromatography

Sources & evidence

ORD record
ord-128bc1dec68f491e8262feb74f36875c
Source dataset
uspto-grants-2013_03
Patent number
US08394853B2

Reaction notes

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