Triphenylphosphine → ((3-Chlorothieno[3,2-b]pyridin-5-yl)methyl)triphenylphosphonium chloride

HRID 2259486Notes

Reaction equation

HRID 2259486 reaction equation
[Cl:1][C:2]1[C:6]2=[N:7][C:8]([CH2:11]Cl)=[CH:9][CH:10]=[C:5]2[S:4][CH:3]=1.[P:13]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CC#N>[Cl-:1].[Cl:1][C:2]1[C:6]2=[N:7][C:8]([CH2:11][P+:13]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[CH:9][CH:10]=[C:5]2[S:4][CH:3]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 190028563-Chloro-5-(chloromethyl)thieno[3,2-b]-pyridine

Product 1

HCID 88252540((3-Chlorothieno[3,2-b]pyridin-5-yl)methyl)triphenylphosphonium chlorideYield 159%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-chloro-5-(chloromethyl)thieno[3,2-b]-pyridine (1.2 g, 5.5 mmol) in CH3CN (20 mL) was added P(Ph)3 (2.88 g, 11 mmol). The mixture was refluxed for 20 hr. and was then evaporated to dryness. Et2O (8 mL) was added. The mixture was stirred vigorously and the crystalline salt was filtered and washed with more Et2O to give. 2.1 g (81%) of the title compound.

Workup

  1. temperatureThe mixture was refluxed for 20 hr
  2. customand was then evaporated to dryness
  3. additionEt2O (8 mL) was added
  4. filtrationthe crystalline salt was filtered
  5. washwashed with more Et2O
  6. customto give

Sources & evidence

ORD record
ord-e9627dcfb2e64002af7c87094f894747
Source dataset
uspto-grants-1995_12
Patent number
US05472964

Reaction notes

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