Water → HCID 23130795, compound

HRID 2080057Notes

Reaction equation

HRID 2080057 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Br:7][C:8]1[CH:9]=[C:10]([CH:19]=[CH:20][CH:21]=1)[O:11][C:12]1[S:16][C:15]([C:17]#[N:18])=[CH:14][CH:13]=1.O>O1CCCC1>[Br:7][C:8]1[CH:9]=[C:10]([CH:19]=[CH:20][CH:21]=1)[O:11][C:12]1[S:16][C:15]([CH2:17][NH2:18])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydride2×HCID 23130511HCID 23130511, compound

Product 1

HCID 23130795HCID 23130795, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Next, to a solution of lithium aluminum hydride (204 mg, 5.39 mmol) in tetrahydrofuran (10 mL) was added a solution of the resulting 5-(3-bromophenoxy)-thiophene-2carbonitrile (1.01 g, 3.59 mmol) in tetrahydrofuran (10 mL), and the solution was stirred at room temperature for 2 hours. Then, lithium aluminum hydride (68 mg, 1.80 mmol) was added, and the solution was further stirred at room temperature for 1 hour. Water was added to the reaction solution, which was then extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and the solvent was evaporated to obtain a mixture of the title compound and debrominated compound (740 mg) as a pale brown oil. As this mixture cannot be purified, it was used in the next reaction without purification.

Workup

  1. stirringthe solution was further stirred at room temperature for 1 hour
  2. extractionwas then extracted with ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated
  5. customto obtain

Sources & evidence

ORD record
ord-4d2a19179c954d28b8f7acff9ccf5da8
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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