Tetramethylenebis[triphenylphosphonium] dibromide → 3-Oxo-2-cyanopropanoic acid ethyl ester tetramethylenebis(triphenylphosphonium) salt

HRID 1454750Notes

Reaction equation

HRID 1454750 reaction equation
[K].[CH2:2]([O:4][C:5](=[O:11])[CH:6]([C:9]#[N:10])[CH:7]=[O:8])[CH3:3].[CH:12]1[CH:17]=[CH:16][C:15]([P+:18]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH2:19][CH2:20][CH2:21][CH2:22][P+:23]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:14][CH:13]=1.[Br-].[Br-]>>[C:30]1([P+:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:22][CH2:21][CH2:20][CH2:19][P+:18]([C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)([C:15]2[CH:14]=[CH:13][CH:12]=[CH:17][CH:16]=2)[C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[CH2:2]([O:4][C:5](=[O:11])[CH:6]([C:9]#[N:10])[CH:7]=[O:8])[CH3:3]

Participants

4

Reactant 3

HCID 3084237Tetramethylenebis[triphenylphosphonium] dibromideHCID 5462222PotassiumHCID 11008001HCID 11008001, compound

Product 1

HCID 876850373-Oxo-2-cyanopropanoic acid ethyl ester tetramethylenebis(triphenylphosphonium) salt

Procedure

CDP-12 was prepared similar to the method used to prepare CDP-2 from potassium salt of 3-oxo-2-cyanopropanoic acid ethyl ester (1.43 g, 8 mmol) and tetramethylenebis(triphenylphosphonium bromide) (2.96 g, 4 mmol) to give the corresponding product in quantitative yield that is hygroscopic.

Workup

  1. customCDP-12 was prepared similar to the method
  2. customto give the corresponding product in quantitative yield that

Sources & evidence

ORD record
ord-8337825c08104c42ac6907c65b312899
Source dataset
uspto-grants-2009_01
Patent number
US07482113B2

Reaction notes

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