Sodium Hydroxide → 2-(5-Oxopentyl)-2-(3,3,3-trifluoropropyl)malononitrile

HRID 1443598Notes

Reaction equation

HRID 1443598 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([CH2:34][CH2:35][C:36]([F:39])([F:38])[F:37])([C:32]#[N:33])[C:30]#[N:31].[OH-].[Na+]>ClCCl>[O:23]=[CH:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([CH2:34][CH2:35][C:36]([F:37])([F:38])[F:39])([C:32]#[N:33])[C:30]#[N:31]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 159087TriacetoxyperiodinaneHCID 588790372-(5-Hydroxypentyl)-2-(3,3,3-trifluoropropyl)malononitrile

Product 1

HCID 588790302-(5-Oxopentyl)-2-(3,3,3-trifluoropropyl)malononitrileYield 67.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

20 ml of a 15% solution of Dess-Martin periodinane=1,1,1-tris(acetyloxy)-1,1-di-hydro-1,2-benziodoxol-3-(1H)-one in dichloromethane was added dropwise to 1.5 g of 2-(5-hydroxypentyl)-2-(3,3,3-trifluoropropyl)malononitrile, and the mixture was stirred at room temperature for 5 hours. Thereafter, the reaction mixture was added to an aqueous dilute sodium hydroxide solution and then extracted with chloroform. The organic layer was washed successively with water and aqueous sodium chloride, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 1.0 g of 2-(5-oxopentyl)-2-(3,3,3-trifluoropropyl)malononitrile.

Workup

  1. extractionextracted with chloroform
  2. washThe organic layer was washed successively with water and aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dff1dd86b8f94604bd39e0facd7e099f
Source dataset
uspto-grants-2010_02
Patent number
US07662402B2

Reaction notes

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