Water → HCID 19001664, compound

HRID 1195307Notes

Reaction equation

HRID 1195307 reaction equation
[CH:1]([C:4]1[C:5]([CH2:13][C:14](O)=[O:15])=[CH:6][C:7]2[O:11][CH2:10][O:9][C:8]=2[CH:12]=1)([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH:1]([C:4]1[C:5]([CH2:13][CH2:14][OH:15])=[CH:6][C:7]2[O:11][CH2:10][O:9][C:8]=2[CH:12]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 19001695HCID 19001695, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19001664HCID 19001664, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 6.25 g of (6-isopropyl-1,3-benzodioxol-5-yl)acetic acid (crude crystal) in 30 ml of tetrahydrofuran was dropwise added to a suspension of 1.6 g of lithium aluminum hydride in 40 ml of tetrahydrofuran under cooling with ice. The obtained mixture was stirred overnight. 1.6 ml of water, 1.6 ml of a 15% aqueous solution of sodium hydroxide and 4.8 ml of water were added to the resulting mixture successively under cooling with ice. The obtained mixture was filtered and the filtrate was concentrated. The residue was purified by silica gel column chromatography to obtain 4.51 g of the title compound as a colorless oil.

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. filtrationThe obtained mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d33a37de706e4fafb5e28cd08c602b18
Source dataset
uspto-grants-1992_05
Patent number
US05110956

Reaction notes

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