Sodium hydride → HCID 15860308, compound

HRID 1291706Notes

Reaction equation

HRID 1291706 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C@@H:10]1[CH2:12][C@H:11]1[C:13]#[N:14].[H-].[Na+].[I-].[CH3:18][S+](C)(C)=O.FC1[CH:29]=[CH:28][C:27]([O:30]C)=CC=1/C=C/C#N.[NH4+].[Cl-]>CS(C)=O.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C@@H:10]1[CH2:12][C@H:11]1[CH2:13][NH:14][C:27](=[O:30])[CH:28]([CH3:18])[CH3:29]

Participants

8

Reactant 5

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 53862340HCID 53862340, compoundHCID 70274102HCID 70274102, compound

Product 1

HCID 15860308HCID 15860308, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

(trans)-2-(2-Fluoro-5-methoxyphenyl)cyclopropane carbonitrile: To a suspension of NaH (1.73 g, 72 mmol) in DMSO (40 mL) was added solid trimethylsulfoxonium iodide (15.9 g, 72 mmol) in small portions. After the foaming had subsided (40 min), a solution of (trans)-3-(2-fluoro-5-methoxyphenyl)-2-propenenitrile (4.26 g, 24 mmol) in DMSO (10 mL) was added dropwise, maintaining the temperature between 35°-40° C. Stirring was continued for 18 h at room temperature, followed by the dropwise addition of saturated NH4Cl (100 mL) and extraction with ethyl acetate. The organics were combined, washed with brine, dried (K2CO3), and concentrated to give a red oil which was then purified by silica gel chromatography (CH2 Cl2 /hexane, 60:40) to afford the title compound as a clear oil (46% yield): 1H NMR (300 MHz, CDCl3) δ0.82-0.88 (m, 2H), 1.65-1.75 (m, 1H), 2.55-2.62 (m, 1H), 3.75 (s, 3H), 6.50-6.55 (m, 1H), 6.60-6.70 (m, 1H), 6.92 (t, J=6.5 Hz, 1H).

Workup

  1. custom(40 min)
  2. temperaturemaintaining the temperature between 35°-40° C
  3. washwashed with brine
  4. dry with materialdried (K2CO3)
  5. concentrationconcentrated
  6. customto give a red oil which
  7. customwas then purified by silica gel chromatography (CH2 Cl2 /hexane, 60:40)

Sources & evidence

ORD record
ord-504e5aa166b747daa8711b26bc6b5149
Source dataset
uspto-grants-1998_05
Patent number
US05753709

Reaction notes

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