Lithium → HCID 67457719, compound

HRID 1713290Notes

Reaction equation

HRID 1713290 reaction equation
[Li].[CH2:2]([O:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:13]#[N:14])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>O1CCCC1>[CH2:2]([O:9][C:10]1[CH:11]=[C:12]([CH2:13][NH2:14])[CH:15]=[CH:16][C:17]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 3028194LithiumHCID 21738733HCID 21738733, compound

Product 1

HCID 67457719HCID 67457719, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

To a suspension of lithium alminiumhydride (0.399 g) in tetrahydrofuran (45 mL) was added dropwise a solution of 3-benzyloxy-4-phenylbenzonitrile (2.00 g) in tetrahydrofuran (25 mL) at room temperature, and the resulting mixture was stirred at 60° C. for 3 hours. The reaction mixture was cooled to room temperature and then quenched by sequential addition of water (0.399 mL), 15% aqueous sodium hydroxide (0.399 mL) and water (0.399 mL). After addition of anhydrous sodium sulfate (20 g), the mixture was stirred at room temperature for 4 hours and the insoluble material was filtered out. The filtrate was concentrated under reduced pressure to give the title compound (1.97 g).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customquenched by sequential addition of water (0.399 mL), 15% aqueous sodium hydroxide (0.399 mL) and water (0.399 mL)
  3. additionAfter addition of anhydrous sodium sulfate (20 g)
  4. stirringthe mixture was stirred at room temperature for 4 hours
  5. filtrationthe insoluble material was filtered out
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3d56cef305234e758cf6cdd478364409
Source dataset
uspto-grants-2010_09
Patent number
US07795236B2

Reaction notes

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