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

HRID 2401914Notes

Reaction equation

HRID 2401914 reaction equation
C[O:2][C:3]([C:5]1[CH:15]=[CH:14][C:8]2[O:9][C:10]([F:13])([F:12])[O:11][C:7]=2[CH:6]=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[F:13][C:10]1([F:12])[O:9][C:8]2[CH:14]=[CH:15][C:5]([CH2:3][OH:2])=[CH:6][C:7]=2[O:11]1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 591292611,3-Benzodioxole-5-carboxylic acid, 2,2-difluoro-, methyl ester

Product 1

HCID 12814281(2,2-Difluoro-1,3-dioxaindan-5-yl)methanolYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Crude 2,2-difluoro-benzo[1,3]dioxole-5-carboxylic acid methyl ester (11.5 g) dissolved in 20 mL of anhydrous tetrahydrofuran (THF) was slowly added to a suspension of lithium aluminum hydride (4.10 g, 106 mmol) in anhydrous THF (100 mL) at 0° C. The mixture was then warmed to room temperature. After being stirred at room temperature for 1 hour, the reaction mixture was cooled to 0° C. and treated with water (4.1 g), followed by sodium hydroxide (10% aqueous solution, 4.1 mL). The resulting slurry was filtered and washed with THF. The combined filtrate was evaporated to dryness and the residue was purified by silica gel column chromatography to give (2,2-difluoro-benzo[1,3]dioxol-5-yl)-methanol (7.2 g, 38 mmol, 76% over two steps) as a colorless oil.

Workup

  1. temperaturethe reaction mixture was cooled to 0° C.
  2. filtrationThe resulting slurry was filtered
  3. washwashed with THF
  4. customThe combined filtrate was evaporated to dryness
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2fc20da5341146f9942e8d2fcdea0774
Source dataset
uspto-grants-2014_08
Patent number
US08796312B2

Reaction notes

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