Methyl bromoacetate → HCID 69066641, compound

HRID 1436873Notes

Reaction equation

HRID 1436873 reaction equation
[C:1]([CH:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:4][CH:5]=[CH2:6])#[N:2].Br[CH2:14][C:15]([O:17][CH3:18])=[O:16]>C1COCC1>[C:1]([C:3]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)([CH2:4][CH:5]=[CH2:6])[CH2:14][C:15]([O:17][CH3:18])=[O:16])#[N:2]

Participants

4

Reactant 2

HCID 60984Methyl bromoacetateHCID 10607021α-2-Propen-1-ylbenzeneacetonitrile

Product 1

HCID 69066641HCID 69066641, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a cooled solution (−78° C.) of 4-cyano-4-phenyl-1-butene (6.23 g, 39.6 mmol) in anhydrous THF was added LIDS (1M in THF, 43.5 mL, 43.5 mmol) dropwise. The solution was stirred at −78° C. for 0.5 hour, then methyl bromoacetate (6.67 g, 43.6 mmol) was added dropwise. After stirring at room temperature for 24 hours, the reaction mixture was concentrated under vacuum. The residual material was purified using silica gel column chromatography eluting with 0-20% EtOAc in hexanes. The appropriate fractions were combined and concentrated to afford the title compound. 1H NMR (400 MHz, DMSO-d6) δ 7.38 (m, 5H), 5.57 (m, 1H), 5.14 (m, 2H), 3.49 (s, 3H), 3.49 (m, 2H), 2.78 (m, 2H) ppm. ES MS M+1=230.

Workup

  1. stirringAfter stirring at room temperature for 24 hours
  2. concentrationthe reaction mixture was concentrated under vacuum
  3. customThe residual material was purified
  4. washeluting with 0-20% EtOAc in hexanes
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-80703499c38049fb9d91efa4e7dd5c9d
Source dataset
uspto-grants-2009_11
Patent number
US07619086B2

Reaction notes

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