HCID 66975468, compound → HCID 66975729, compound

HRID 1022640Notes

Reaction equation

HRID 1022640 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH:12]2[CH2:16][O:15][C:14]([CH3:18])([CH3:17])[O:13]2)[C:10]#[N:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH:12]2[CH2:16][O:15][C:14]([CH3:18])([CH3:17])[O:13]2)[CH2:10][NH2:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 66975468HCID 66975468, compoundHCID 86583787Diisobutylaluminumhydride toluene

Product 1

HCID 66975729HCID 66975729, compoundYield 100.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of (2RS)-(3,4-dichlorophenyl)[(4RS)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanenitrile (10.0 g) in toluene (100 ml) was added dropwise 1.5 M diisobutylaluminum hydride/toluene solution (51.3 under nitrogen purging at −78° C., and the mixture was stirred for 3 hr. The reaction was quenched with water at −78° C., aqueous potassium carbonate solution was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated to give the title compound (10.2 g) as a colorless oil. This was used for the next step without purification.

Workup

  1. customThe reaction was quenched with water at −78° C.
  2. additionaqueous potassium carbonate solution was added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-9bb153d0edb745fdb959eb98c2463100
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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