Triethylamine → Methyl 2-(4-(cyanomethyl)benzyl)-3-oxobutanoate

HRID 445045Notes

Reaction equation

HRID 445045 reaction equation
[OH:1][CH:2]([CH3:9])[C:3](=[CH2:8])[C:4]([O:6][CH3:7])=[O:5].Br[C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]#[N:19])=[CH:13][CH:12]=1.C(N(CC)CC)C>C(#N)C.C1(C)C=CC=CC=1.O>[C:18]([CH2:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:8][CH:3]([C:2](=[O:1])[CH3:9])[C:4]([O:6][CH3:7])=[O:5])=[CH:12][CH:13]=1)#[N:19]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 27914Benzeneacetonitrile, 4-bromo-HCID 5080248Methyl 3-hydroxy-2-methylen-butanoat

Product 1

HCID 59590640Methyl 2-(4-(cyanomethyl)benzyl)-3-oxobutanoate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

A stirred mixture of methyl 3-hydroxy-2-methylenebutanoate (70.0 g), 2-(4-bromophenyl)acetonitrile (126.5 g), PdCl2[P(o-tol)3]2 (4.2 g) and triethylamine (108.9 g) in acetonitrile (280 mL) was heated under nitrogen at 70° C. for 6 hours. The mixture was cooled to room temperature, diluted with toluene (840 mL) and water (840 mL) and stirred for 10 minutes. The organic layer was separated, washed with water (840 mL) and concentrated under reduced pressure to give the subtitle compound as a red oil, 158.7 g. This product was used in the next step without further purification.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customThe organic layer was separated
  3. washwashed with water (840 mL)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a8d6376f78754e45938942e10dfc0e61
Source dataset
uspto-grants-2013_07
Patent number
US08476288B2

Reaction notes

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