Sodium hydride → HCID 57460183, compound

HRID 1673681Notes

Reaction equation

HRID 1673681 reaction equation
[CH3:1][O:2][CH2:3][C:4](=[O:10])[CH2:5][C:6]([O:8][CH3:9])=[O:7].[H-].[Na+].Br[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[C:22]([C:27]#[N:28])=[CH:23][CH:24]=[CH:25][CH:26]=2)=[CH:17][CH:16]=1>O1CCCC1>[C:27]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[C:18]1[CH:17]=[CH:16][C:15]([CH2:14][CH:5]([C:4](=[O:10])[CH2:3][O:2][CH3:1])[C:6]([O:8][CH3:9])=[O:7])=[CH:20][CH:19]=1)#[N:28]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 123500Methyl 4-methoxyacetoacetateHCID 15019124'-(Bromomethyl)-2-cyanobiphenyl

Product 1

HCID 57460183HCID 57460183, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of methyl 4-methoxy-3-oxobutyrate (10.7 g) in tetrahydrofuran (150 mL) was added to a mixture of sodium hydride (1.91 g) and tetrahydrofuran (150 mL) at room temperature, and the mixture was stirred at room temperature for 30 min. 4′-(Bromomethyl)biphenyl-2-carbonitrile (10 g) was added to the reaction mixture, and the reaction mixture was stirred at room temperature for 3 days. The reaction mixture was concentrated. To the residue were added 5% aqueous potassium hydrogen sulfate solution and then ethyl acetate, and the mixture was extracted. The ethyl acetate layer was washed with saturated brine and concentrated. The residue was purified by silica gel column chromatography to give the title compound as a colorless oil (12.1 g, 98%).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 3 days
  2. concentrationThe reaction mixture was concentrated
  3. additionTo the residue were added 5% aqueous potassium hydrogen sulfate solution
  4. extractionethyl acetate, and the mixture was extracted
  5. washThe ethyl acetate layer was washed with saturated brine
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e6ce2a1ca69f4e3fb997b8adde96c74d
Source dataset
uspto-grants-2011_08
Patent number
US07998968B2

Reaction notes

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