Sodium Bicarbonate → HCID 178511233, compound

HRID 486368Notes

Reaction equation

HRID 486368 reaction equation
[Cl-].[F:2][C:3]1[CH:4]=[C:5]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)=[CH:12][N:11]=2)[CH:6]=[CH:7][C:8]=1[F:9].[CH:36]([C@H:38]1[CH2:43][CH2:42][C@H:41]([C:44]#[N:45])[CH2:40][CH2:39]1)=O.C(=O)([O-])O.[Na+]>C(OCC)C>[F:2][C:3]1[CH:4]=[C:5]([C:10]2[CH:15]=[CH:14][C:13]([CH:16]=[CH:36][C@H:38]3[CH2:43][CH2:42][C@H:41]([C:44]#[N:45])[CH2:40][CH2:39]3)=[CH:12][N:11]=2)[CH:6]=[CH:7][C:8]=1[F:9]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 19094917[2-(3,4-Difluorophenyl)-5-pyridyl]methyltriphenylphosphonium chlorideHCID 178511250HCID 178511250, compound

Product 1

HCID 178511233HCID 178511233, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

A suspension of 12.05 g of [2-(3,4-difluorophenyl)-5-pyridyl]methyltriphenylphosphonium chloride in 70 ml of diethyl ether is treated with 2.67 g of potassium tert.-butylate in a nitrogen atmosphere. The dark yellow suspension is stirred at room temperature for a further 30 minutes. A solution of 2.74 g of -trans-4-formylcyclohexanecarbonitrile in 30 ml of diethyl ether is then added dropwise at 0° C. The reaction mixture is stirred at 0° C. for a further 1 hour, then stirred with 40 ml of 1N sodium hydrogen carbonate solution and diluted with diethyl ether. The organic phase is separated, washed neutral with water, dried over sodium sulphate and concentrated. The residue is chromatographed on silica gel with hexane/ethyl acetate 3:1 (v/v). There is obtained trans-4-[2-[2-(3,4-difluorophenyl)-5-pyridyl]vinyl]cyclohexanecarbonitrile.

Workup

  1. stirringThe reaction mixture is stirred at 0° C. for a further 1 hour
  2. customThe organic phase is separated
  3. washwashed neutral with water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated
  6. customThe residue is chromatographed on silica gel with hexane/ethyl acetate 3:1 (v/v)

Sources & evidence

ORD record
ord-9063d873f1734488861de93a2223ddeb
Source dataset
uspto-grants-1994_03
Patent number
US05292452

Reaction notes

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