Methanol → HCID 28409843, compound

HRID 2080052Notes

Reaction equation

HRID 2080052 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([CH:13]([O:15][C:16]2[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=2)[CH3:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CO.[Cl-].[NH4+]>O1CCCC1.O.C(OCC)(=O)C>[C:7]1([C@@H:13]([O:15][C:16]2[CH:17]=[CH:18][C:19]([CH2:20][NH2:21])=[CH:22][CH:23]=2)[CH3:14])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 21711561HCID 21711561, compound

Product 1

HCID 28409843HCID 28409843, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Next, to a solution of lithium aluminum hydride (68 mg, 1.78 mmol) in tetrahydrofuran (5.0 mL) was added a solution of the resulting 4-(1-phenyl-ethoxy)-benzonitrile (159 mg, 0.712 mmol) in tetrahydrofuran (1 mL) on an ice bath, which was stirred under reflux for 2 hours. The reaction solution was allowed to room temperature, a mixture solvent of methanol and water (9:1) was added, an aqueous solution of saturated ammonium chloride was further added, then, ethyl acetate and water were added for partitioning, the organic layer was dried over anhydrous magnesium sulfate, then, the solvent was evaporated to obtain the title compound (172 mg, quantitatively) as a yellow oily substance.

Workup

  1. temperatureunder reflux for 2 hours
  2. customwas allowed to room temperature
  3. customfor partitioning
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-bdf2f796fe2842d8a1ce5d9b34a9114a
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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