Hydrochloric Acid → Ethyl 2-cyano-3,3-dimethyl-4-phenylbutanoate

HRID 1886894Notes

Reaction equation

HRID 1886894 reaction equation
[C:1]([C:3](=[C:9]([CH3:11])[CH3:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].[CH2:12]([Mg]Cl)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl>CCOCC>[C:1]([CH:3]([C:9]([CH3:10])([CH3:11])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1365732-Cyano-3-methyl-but-2-enoic acid ethyl esterHCID 178418336HCID 178418336, compound

Product 1

HCID 236365Ethyl 2-cyano-3,3-dimethyl-4-phenylbutanoateYield 73.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of ethyl 2-cyano-3-methylbut-2-enoate (0.91 mL, 6 mmol) in ether (4 mL) under N2 was added 1.0 M benzylmagnesium chloride in ether (9 mL, 9 mmol) dropwise to give a pale yellow solution. The reaction was stirred at room temperature for 3 h, and was then cooled to 0° C. and acidified with 10% HCl (10 mL). The organic layer was isolated, washed with water and brine, dried over Na2SO4, and concentrated under reduced pressure to give bright yellow oil. Purification by flash column chromatography (10% ethyl acetate in hexanes, Rf=0.26) gave the title compound as a pale yellow oil (1.08 g, 73.5%). 1H NMR (500 MHz, CDCl3) δ 8.02 (d, J=7.6 Hz, 1H), 7.51 (t, J=7.6 Hz, 1H), 7.32 (t, J=7.6 Hz, 1H), 7.22 (d, J=7.6 Hz, 2H), 4.22 (m, 2H), 3.44 (s, 1H), 3.07 (d, J=16.5 Hz, 1H), 2.83 (d, J=16.5 Hz, 1H), 1.28 (t, J=7.1 Hz, 2H), 1.18 (s, 3H), 1.15 (s, 3H).

Workup

  1. customto give a pale yellow solution
  2. temperaturewas then cooled to 0° C.
  3. customThe organic layer was isolated
  4. washwashed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customto give bright yellow oil
  8. customPurification by flash column chromatography (10% ethyl acetate in hexanes, Rf=0.26)

Sources & evidence

ORD record
ord-1a701e5207784c708527746358b7f771
Source dataset
uspto-grants-2013_08
Patent number
US08501722B2

Reaction notes

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