Sodium Chloride → HCID 57809879, compound

HRID 2106041Notes

Reaction equation

HRID 2106041 reaction equation
COC(=O)[CH:4]([C:17]#[N:18])[C:5]1([CH3:16])[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([F:15])[CH:13]=2)[O:8][CH2:7][CH2:6]1.[Cl-].[Na+]>CS(C)=O.O>[F:15][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[O:8][CH2:7][CH2:6][C:5]2([CH2:4][C:17]#[N:18])[CH3:16]

Participants

5

Reactant 2

HCID 5234Sodium ChlorideHCID 57809752HCID 57809752, compound

Product 1

HCID 57809879HCID 57809879, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A mixture of 3.1 g (11.8 mmol) of cyano-(6-fluoro-4-methylchroman4-yl)acetic acid methyl ester and 2.47 g (42.4 mmol) of sodium chloride in 30 mL of wet DMSO was warmed to reflux. The reaction was monitored by TLC. After 4 hours, the reaction was cooled and diluted with water and extracted with diethyl ether. The combined organic layers were washed with four portions of water, brine, dried over magnesium sulfate, and concentrated in vacuo to afford 2.1 g (87%) of (6-fluoro-4-methylchroman-4-yl)acetonitrile as an oil.

Workup

  1. temperaturewas warmed to reflux
  2. temperaturethe reaction was cooled
  3. extractionextracted with diethyl ether
  4. washThe combined organic layers were washed with four portions of water, brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8aaea83030f3457b9223d9a1d5274e9d
Source dataset
uspto-grants-2009_08
Patent number
US07579469B2

Reaction notes

Loading…