Hydrochloric Acid → HCID 21217960, compound

HRID 1586226Notes

Reaction equation

HRID 1586226 reaction equation
[H-].[Na+].[C:3]([C:5]1[CH:6]=[C:7]([CH:11]([OH:19])[CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:8]=[CH:9][CH:10]=1)#[N:4].[CH:20]1[C:25]([CH2:26]Br)=[CH:24][CH:23]=[C:22]([C:28]#[N:29])[CH:21]=1.[I-].[K+].Cl>CCCCCC.CN(C=O)C.C(OCC)(=O)C>[C:3]([C:5]1[CH:6]=[C:7]([CH:11]([O:19][CH2:26][C:25]2[CH:24]=[CH:23][C:22]([C:28]#[N:29])=[CH:21][CH:20]=2)[CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:8]=[CH:9][CH:10]=1)#[N:4]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 24758Sodium hydrideHCID 869964-(Bromomethyl)benzonitrileHCID 21217922HCID 21217922, compound

Product 1

HCID 21217960HCID 21217960, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Part C. Sodium hydride (0.76 mmol) (washed free of the mineral oil with hexane) was added to a solution of ethyl 3-(cyano)-gamma-(hydroxy)benzenebutanoate (0.15 gm, 0.64 mmol), a-bromo-p-tolunitrile (0.125 gm, 0.64 mmol) and potassium iodide in 5 mL DMF at 0° C. under a nitrogen atmosphere. The reaction was stirred for 2 hrs at 0° C. and was allowed to stir at ambient temperature overnight. The reaction solution was poured into 1N HCl and extracted with ethyl acetate. The combined organic layer was washed with water, brine, dried over magnesium sulfate and concentrated to give the crude product as a viscous oil. The product was purified by flash chromatography on silica gel (75 mL) eluting toluene:ethyl acetate (v:v, 90:10) to give ethyl 3-(cyano)-gamma-[[4-(cyano)phenyl]methoxy]benzenebutanoate as a semisolid residue 0.10 gm (45% yield) MS 366(M+NH4)+ 1 H NMR (CDCl3): 7.72-7.47(m, 6H), 7.42(d, 2H), 4.5-4.3(m, 3H), 4.1(q, 2H), 2.42(m, 2H), 2.17-1.97(m, 2H), 1.23(t, 3H).

Workup

  1. stirringto stir at ambient temperature overnight
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layer was washed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customto give the crude product as a viscous oil
  7. customThe product was purified by flash chromatography on silica gel (75 mL)
  8. washeluting toluene

Sources & evidence

ORD record
ord-c50b19648aad4f43a2d1631436c3a16e
Source dataset
uspto-grants-1999_08
Patent number
US05942544

Reaction notes

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