Water → HCID 23130573, compound

HRID 2080088Notes

Reaction equation

HRID 2080088 reaction equation
[CH2:1]([O:8][N:9]1[CH:13]=[CH:12][C:11]([CH:14]=[O:15])=[CH:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.C(OCC)(=O)C>O1CCCC1>[CH2:1]([O:8][N:9]1[CH:13]=[CH:12][C:11]([CH2:14][OH:15])=[CH:10]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 23130676HCID 23130676, compound

Product 1

HCID 23130573HCID 23130573, compoundYield 33.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-benzyloxy-1H-pyrrole-3-carbaldehyde described in Preparation Example 63 (500 mg, 2.5 mmol) in tetrahydrofuran (10 mL) was added lithium aluminum hydride (75 mg, 1.97 mmol), and the solution was stirred at room temperature for 10 minutes. Water and ethyl acetate were added to the reaction solution, which was then partitioned, silica gel was added to the organic layer, the solvent was evaporated in vacuo for adsorption, purification by silica gel column chromatography (hexane:ethyl acetate=2:1) was carried out, and the title compound (168 mg, 0.828 mmol, 33.1%) was obtained as a colorless oil.

Workup

  1. customwas then partitioned
  2. additionsilica gel was added to the organic layer
  3. customthe solvent was evaporated in vacuo for adsorption, purification by silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-91ccde472a084836befb74c7a964d466
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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