Ethyl Acetate → HCID 67103340, compound

HRID 2080779Notes

Reaction equation

HRID 2080779 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9](=O)[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:17]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:18][C:19]2[N:20]([CH3:24])[CH:21]=[CH:22][N:23]=2)=[CH:12][CH:11]=1.C(OCC)(=O)C.C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>C1COCC1.CO>[C:28]([O:27][C:25](=[O:26])[N:17]([CH2:16][C:13]1[CH:12]=[CH:11][C:10]([CH2:9][OH:8])=[CH:15][CH:14]=1)[CH2:18][C:19]1[N:20]([CH3:24])[CH:21]=[CH:22][N:23]=1)([CH3:31])([CH3:29])[CH3:30]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydrideHCID 67103861HCID 67103861, compound

Product 1

HCID 67103340HCID 67103340, compoundYield 46.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (1.0 g) was suspended in THF (95 ml). After that, a THF solution (95.1 ml) containing the compound (3.17 g) obtained in Example 21-1 was gradually dropped therein at room temperature. Then, the whole was stirred for additional 1 hour. The reaction solution was added with ethyl acetate, methanol, and a 10% aqueous sodium potassium tartrate solution and the whole was stirred for 1 hour, followed by extraction with chloroform. The organic layer was dried with anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified through silica gel column chromatography (chloroform/methanol), thereby obtaining the subject compound (1.37 g) as a brown oily substance.

Workup

  1. additionwas gradually dropped
  2. customat room temperature
  3. extractionfollowed by extraction with chloroform
  4. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified through silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-da81218aa62543e48174c6e826cce27d
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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