Water → HCID 21217975, compound

HRID 1586225Notes

Reaction equation

HRID 1586225 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=[O:7])#[N:2].C(OC1(O[Si:18]([CH3:21])([CH3:20])[CH3:19])CC1)C.O.[C:23]([O:26][CH2:27][CH3:28])(=[O:25])[CH3:24].[CH2:29](Cl)Cl>[I-].[Zn+2].[I-]>[C:1]([C:3]1[CH:4]=[C:5]([CH:6]([O:7][Si:18]([CH3:21])([CH3:20])[CH3:19])[CH2:29][CH2:24][C:23]([O:26][CH2:27][CH3:28])=[O:25])[CH:8]=[CH:9][CH:10]=1)#[N:2]

Participants

7

Reactant 5

HCID 962WaterHCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 90670m-FormylbenzonitrileHCID 2734686(1-Ethoxycyclopropoxy)trimethylsilane

Product 1

HCID 21217975HCID 21217975, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 9883512zinc(II)iodideCatalyst

Procedure

Part A. A mixture of 3-cyanobenzaldehyde (2.0 gm, 15.2 mmol), 1-ethoxy-1-trimethylsilyloxycyclopropane (3.44 gm, 19.73 mmol) and zinc iodide (0.12 gm, 0.38 mmol) in 30 mLs methylene chloride under a nitrogen atmosphere was stirred at ambient temperature for 18 hrs. The reaction mixture was poured into water and extracted with methylene chloride. The combined organic layers was washed with water, brine, dried over magnesium sulfate and concentrated to give the crude product as a yellow oil. The oil was purified by flash chromatography on silica gel (100 mLs) eluting hexane:ethyl acetate (v:v, 90:10) to give ethyl 3-(cyano)-gamma-(trimethylsilyloxy)benzenebutanoate as a viscous oil 1.75 gm (38% yield) MS 323(M+H)+, 1H NMR (CDCl3) 7.8(s, 1H), 7.5(d, 2H), 7.39(t, 1H), 4.73(m, 1H), 4.07(q, 2H), 2.41-2.2 (m, 2H), 2.0-1.8(m, 2H), 1.20(t, 3H), 0.03 (s, 9H).

Workup

  1. extractionextracted with methylene chloride
  2. washThe combined organic layers was washed with water, brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customto give the crude product as a yellow oil
  6. customThe oil was purified by flash chromatography on silica gel (100 mLs)
  7. washeluting hexane

Sources & evidence

ORD record
ord-a79cc20da2c7497084d09f700ca24330
Source dataset
uspto-grants-1999_08
Patent number
US05942544

Reaction notes

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