Sodium Hydroxide → 3-((Tert-butyldiphenylsilyl)oxy)-2-fluoropropan-1-OL

HRID 1847020Notes

Reaction equation

HRID 1847020 reaction equation
C([O:3][C:4](=O)[CH:5]([F:25])[CH2:6][O:7][Si:8]([C:21]([CH3:24])([CH3:23])[CH3:22])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)C.[BH4-].[Li+].[OH-].[Na+]>O1CCCC1>[Si:8]([O:7][CH2:6][CH:5]([F:25])[CH2:4][OH:3])([C:21]([CH3:24])([CH3:22])[CH3:23])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 4148881Lithium borohydrideHCID 867249473-{[tert-Butyl(diphenyl)silyl]oxy}-2-fluoropropionic acid ethyl ester

Product 1

HCID 579797963-((Tert-butyldiphenylsilyl)oxy)-2-fluoropropan-1-OLYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-{[Tert-butyl(diphenyl)silyl]oxy}-2-fluoropropionic acid ethyl ester (17.98 g, 48.01 mmol) was dissolved in tetrahydrofuran (250 ml). Lithium borohydride (2.32 g, 96.02 mmol) was added to the solution under cooling on ice and the mixture was stirred for 24 hours. To the reaction solution was added 1N sodium hydroxide aqueous solution under cooling on ice to quench the reaction. The resulting solution was extracted with ethyl acetate, and the resultant was washed with saturated sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to yield 12.10 g (76%) of the title compound in the form of a colorless clear oily product.

Workup

  1. temperatureunder cooling on ice
  2. temperatureunder cooling on ice
  3. customto quench
  4. customthe reaction
  5. extractionThe resulting solution was extracted with ethyl acetate
  6. washthe resultant was washed with saturated sodium chloride solution
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. customthe solvent was removed under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-a2b18fc857254f099700312549946935
Source dataset
uspto-grants-2015_02
Patent number
US08952010B2

Reaction notes

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