Water → (2,2-Difluoro-1,3-dioxaindan-5-yl)methanol

HRID 1610342Notes

Reaction equation

HRID 1610342 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1([F:20])[O:12][C:11]2[CH:13]=[CH:14][C:15]([C:17](O)=[O:18])=[CH:16][C:10]=2[O:9]1.O.[OH-].[Na+]>O1CCCC1>[F:20][C:8]1([F:7])[O:12][C:11]2[CH:13]=[CH:14][C:15]([CH2:17][OH:18])=[CH:16][C:10]=2[O:9]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 6087722,2-Difluoro-1,3-benzodioxole-5-carboxylic acidHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 12814281(2,2-Difluoro-1,3-dioxaindan-5-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (1.86 g, 48.9 mmol) in tetrahydrofuran (30 ml) was dropwise added a solution of 2,2-difluoro-1,3-benzodioxole-5-carboxylic acid (4.942 g, 24.45 mmol) in tetrahydrofuran (30 ml) under ice-cooling and the mixture was stirred at room temperature for 1 hr. The reaction solution was ice-cooled and water (2 ml), 15% aqueous sodium hydroxide solution (2 ml) and water (5 ml) was dropwise added successively to decompose excess lithium aluminum hydride. The mixture was stirred as it was at room temperature for 2 hrs. The resulting-precipitate was removed by filtration and the precipitate was washed with ethyl acetate. The solvent of the collected filtrate was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=6/1−1/1) to give the objective substance.

Workup

  1. temperaturecooling
  2. temperaturecooled
  3. stirringThe mixture was stirred as it
  4. waitwas at room temperature for 2 hrs
  5. customThe resulting-precipitate was removed by filtration
  6. washthe precipitate was washed with ethyl acetate
  7. customThe solvent of the collected filtrate was evaporated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=6/1−1/1)
  9. customto give the objective substance

Sources & evidence

ORD record
ord-30a1d55276474b3195226883b61eedbb
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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