Water → HCID 19001690, compound

HRID 2259757Notes

Reaction equation

HRID 2259757 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([C:9]1[C:10]([CH2:18][C:19](O)=[O:20])=[CH:11][C:12]2[O:16][CH2:15][O:14][C:13]=2[CH:17]=1)[CH3:8].O>O1CCCC1>[CH2:7]([C:9]1[C:10]([CH2:18][CH2:19][OH:20])=[CH:11][C:12]2[O:16][CH2:15][O:14][C:13]=2[CH:17]=1)[CH3:8]

Participants

5

Reactant 3

HCID 962WaterHCID 19001614HCID 19001614, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19001690HCID 19001690, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

62 g of lithium aluminum hydride was suspended in 1.5 l of anhydrous tetrahydrofuran. A solution of 200 g of (6-ethyl-1,3-benzodioxol-5-yl)acetic acid in 200 ml of tetrahydrofuran was added dropwise to the suspension and the reaction was conducted at room temperature for 12 h. After the completion of the reaction, water was added thereto and the precipitate was filtered off. The filtrate was concentrated under reduced pressure and water was added to the residue. After extraction with ethyl acetate, the extract was washed with water, dried over magnesium sulfate, concentrated under reduced pressure and purified according to silica gel column chromatography (ethyl acetate/hexane=1:4) to obtain 169 g of the intended compound in the form of a faint yellow oil.

Workup

  1. additionwas added
  2. filtrationthe precipitate was filtered off
  3. concentrationThe filtrate was concentrated under reduced pressure and water
  4. additionwas added to the residue
  5. extractionAfter extraction with ethyl acetate
  6. washthe extract was washed with water
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. custompurified

Sources & evidence

ORD record
ord-17f326b9f01a4a109c4405e2e469a078
Source dataset
uspto-grants-1995_12
Patent number
US05475024

Reaction notes

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