HCID 12750603, compound → HCID 15288194, compound

HRID 1648471Notes

Reaction equation

HRID 1648471 reaction equation
[S:1]1[C:5]2[C:6](=O)[NH:7][C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[CH2:10][C:4]=2[CH:3]=[CH:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[S:1]1[C:5]2[CH2:6][NH:7][C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[CH2:10][C:4]=2[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 12750603HCID 12750603, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 15288194HCID 15288194, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 2.0 g of the product of Example 6 and 500 mg of lithium aluminum hydride in 200 ml of tetrahydrofuran is refluxed for 4 hours. The reaction mixture is carefully quenched with ice cold water and extracted with chloroform. The organic layer is washed well with water, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to a residue. The residue is purified by column chromatography on silica gel by elution with 30% ethyl acetatehexane to give 1.2 g of the desired product as a bright yellow solid, M+ =202.

Workup

  1. customThe reaction mixture is carefully quenched with ice cold water
  2. extractionextracted with chloroform
  3. washThe organic layer is washed well with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo to a residue
  7. customThe residue is purified by column chromatography on silica gel by elution with 30% ethyl acetatehexane

Sources & evidence

ORD record
ord-8d223870514e4a46913bb5148a90057e
Source dataset
uspto-grants-1995_07
Patent number
US05436333

Reaction notes

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