HCID 2598681, compound → HCID 13467414, compound

HRID 1180134Notes

Reaction equation

HRID 1180134 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=O)[CH:6]=[CH:7][CH:8]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 2598681HCID 2598681, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 13467414HCID 13467414, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(3-methoxyphenyl)-N-phenylacetamide (2.0 g, 8.3 mmol) in anhydrous tetrahydrofuran (30 mL) under nitrogen was added lithium aluminum hydride (1.59 g, 42 mmol) in small portions over a 1 hour period. After 16 hours, the reaction was poured over ice and the crude product extracted with ethyl acetate (2×100 mL). The organic layer was dried over MgSO4, filtered and concentrated to provide the title compound (1.3 g, 69% yield): EI-MS (m/z) 227.

Workup

  1. additionthe reaction was poured over ice
  2. extractionthe crude product extracted with ethyl acetate (2×100 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a415051544ae44e09f2a67fe15daac34
Source dataset
uspto-grants-2007_10
Patent number
US07279489B2

Reaction notes

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