Methanol → HCID 59305338, compound

HRID 2240937Notes

Reaction equation

HRID 2240937 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][Si](C)(C)C)=[CH:4][C:3]=1[CH2:14][CH2:15][CH2:16][C:17]#[N:18].CO.C(=O)([O-])[O-].[Cs+].[Cs+]>C(Cl)Cl.C(OCC)C>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([CH2:14][CH2:15][CH2:16][C:17]#[N:18])[CH:4]=1)#[CH:9]

Participants

6

Reactant 3

HCID 887MethanolHCID 10796Cesium carbonateHCID 593053672-Fluoro-5-[2-(trimethylsilyl)ethynyl]benzenebutanenitrile

Product 1

HCID 59305338HCID 59305338, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-(2-Fluoro-5-trimethylsilanylethynyl-phenyl)-butyronitrile (0.27 g, 1.04 mmol), in dry methylene chloride (2.5 mL) and methanol (2.5 mL) was added cesium carbonate (0.41 g, 1.2 mmol) and stirred for 2 h under a nitrogen atmosphere. The mixture was diluted with diethyl ether (15 mL), and partitioned between diethyl ether and H2O (10 mL), and the aqueous layer was extracted with diethyl ether (10 mL), washed with brine and dried over MgSO4, filtered and concentrated in vacuo. Purification by flash chromatography (5-10% ethyl acetate/petroleum ether) gave the title compound as a brown semi solid (0.154 g, 79%), identified by NMR and mass spectral analyses. MS (EI+): 187 (M+).

Workup

  1. custompartitioned between diethyl ether and H2O (10 mL)
  2. extractionthe aqueous layer was extracted with diethyl ether (10 mL)
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography (5-10% ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-cd22060ebe5a44fb8c6bedaa4f52523f
Source dataset
uspto-grants-2010_05
Patent number
US07723368B2

Reaction notes

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