Ethyl bromoacetate → HCID 86657404, compound

HRID 400551Notes

Reaction equation

HRID 400551 reaction equation
[C:1](=[C:4]([C:7]#[N:8])[C:5]#[N:6])([CH3:3])[CH3:2].Br[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12]>[Zn].C1COCC1>[C:5]([CH:4]([C:7]#[N:8])[C:1]([CH3:3])([CH3:2])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])#[N:6]

Participants

5

Reactant 2

HCID 7748Ethyl bromoacetateHCID 533473Isopropylidenemalononitrile

Product 1

HCID 86657404HCID 86657404, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Zinc powder (1.23 g, 18.85 mmol) was added to a THF (20 mL) solution of isopropylidenemalononitrile (1.0 g, 9.42 mmol), ethyl bromoacetate (3.15 g, 18.85 mmol) and titanium bis(cyclopentadienyl)dichloride (235 mg, 0.94 mmol). After stirring for 1 hour the solution was partitioned between ethyl acetate and aqueous 1N HCl. The organic phase was washed with water, brine, dried over MgSO4 and filtered. The solution was concentrated and the crude residue purified by silica gel chromatography using a hexanes/EtOAc gradient to give the indicated product. 1H NMR (400 MHz, CD3CN): δ 4.55 (s, 1H); 4.10 (q, J=7.2 Hz, 2H); 2.48 (s, 2H); 1.24 (s, 6H); 1.21 (t, J=7.2 Hz, 3H).

Workup

  1. customwas partitioned between ethyl acetate and aqueous 1N HCl
  2. washThe organic phase was washed with water, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationThe solution was concentrated
  6. customthe crude residue purified by silica gel chromatography
  7. customto give the indicated product

Sources & evidence

ORD record
ord-056a7d17be4143729c1f902598e7527c
Source dataset
uspto-grants-2014_06
Patent number
US08741910B2

Reaction notes

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