Sodium Hydroxide → (R)-2-chloro-6-(oxiran-2-ylmethoxy)benzonitrile

HRID 2302175

Reaction equation

HRID 2302175 reaction equation
[Cl:1][C:2]1[C:3]([C:9]#[N:10])=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[CH2:13]1[O:15][C@H:14]1[CH2:16]OS(C1C=C([N+]([O-])=O)C=CC=1)(=O)=O.[OH-].[Na+]>CN(C)C=O.CCCCCC.CCOCC>[CH2:16]([O:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[C:9]#[N:10])[C@@H:14]1[O:15][CH2:13]1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 146513Benzenesulfonic acid, 3-nitro-, (2R)-2-oxiranylmethyl esterHCID 44079952-Chloro-6-hydroxybenzonitrile

Product 1

HCID 44186486(R)-2-chloro-6-(oxiran-2-ylmethoxy)benzonitrile

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

3-Chloro-2-cyanophenol (0.55 g, 3.58 mmol) was dissolved in 10 mL of dimethylformamide, and the solution cooled to 0° C. Sodium hydride (0.158 g, 3.94 mmol 60% in oil), washed with hexane and dimethylformamide, was added to cooled solution over a period of one minute. After stirring for 10 minutes at room temperature, (2R)-(−)-glycidyl 3-nitrobenzenesulfonate was added and stirred 16 hours. The reaction was poured into ether and dilute sodium hydroxide. The ether layer was separated and the aqueous layer extracted once more with ether. The combined ether extracts were washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to give 0.7 g of (R)-3-chloro-2-cyanophenyl glycidyl ether.

Workup

  1. additionwas added
  2. temperatureto cooled solution over a period of one minute
  3. stirringstirred 16 hours
  4. customThe ether layer was separated
  5. extractionthe aqueous layer extracted once more with ether
  6. washThe combined ether extracts were washed with water and saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-aa37df42a62c413bb4bf456c9464022b
Source dataset
uspto-grants-2002_08
Patent number
US06432656B1

Linked notes

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