Diethyl Ether → HCID 18448422, compound

HRID 1269653Notes

Reaction equation

HRID 1269653 reaction equation
[CH3:1][C:2]1[C:7]([NH:8][C:9](=O)[CH2:10][CH2:11][CH3:12])=[CH:6][CH:5]=[CH:4][C:3]=1[C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].CCOCC.[OH-].[Na+]>O1CCCC1.O>[CH2:9]([NH:8][C:7]1[C:2]([CH3:1])=[C:3]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[CH:4]=[CH:5][CH:6]=1)[CH2:10][CH2:11][CH3:12]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 18448416HCID 18448416, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18448422HCID 18448422, compoundYield 92.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To solution of N-(2,4′-dimethyl-1,1′-biphenyl-3-yl)butanamide (15 g, 0.056 mol) in anhydrous tetrahydrofuran (500 ml) was added dropwise lithiumaluminium hydride (1 M solution in ether; 112 ml) under nitrogen. The resultant mixture was heated at 75° C. for 5.5 h then allowed to cool to room temperature for 16 h. To the reaction mixture was added dropwise wet ether (50 ml), then 2M NaOH (50 ml) and water (50 ml). The mixture was filtered, the solid residues washed with ether and the filtrate dried (Na2SO4), and the solvents removed in vacuo. The residue was partitioned between CH2Cl2 (400 ml) and water (20 ml). The CH2Cl2 layer was dried (Na2SO4) and the solvent removed in vacuo to afford the title compound as a yellow oil (13.12 g).

Workup

  1. filtrationThe mixture was filtered
  2. washthe solid residues washed with ether
  3. dry with materialthe filtrate dried (Na2SO4)
  4. customthe solvents removed in vacuo
  5. customThe residue was partitioned between CH2Cl2 (400 ml) and water (20 ml)
  6. dry with materialThe CH2Cl2 layer was dried (Na2SO4)
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-c5c621b81ef3435491a1228e568c336b
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Reaction notes

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