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

HRID 1855226Notes

Reaction equation

HRID 1855226 reaction equation
[F:1][C:2]1([F:15])[O:6][C:5]2[CH:7]=[CH:8][C:9]([C:11](OC)=[O:12])=[CH:10][C:4]=2[O:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[F:15][C:2]1([F:1])[O:6][C:5]2[CH:7]=[CH:8][C:9]([CH2:11][OH:12])=[CH:10][C:4]=2[O:3]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)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Methyl 2,2-difluorobenzo[d][1,3]dioxole-5-carboxylate from previous step (11.5 g) dissolved in anhydrous tetrahydrofuran (20 mL) 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 and stirred at for 1 h. 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-difluorobenzo[d][1,3]dioxol-5-yl)methanol as a colorless oil (7.2 g, 76% over two steps).

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-9482be2e5a914cd1ba9d5d1fde55cf9b
Source dataset
uspto-grants-2015_02
Patent number
US08962856B2

Reaction notes

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