Sodium Hydroxide → HCID 57706195, compound

HRID 1662401Notes

Reaction equation

HRID 1662401 reaction equation
[CH3:1][C:2]([C:5]([C:7]1[CH:12]=[C:11]([C:13](OC)=[O:14])[CH:10]=[CH:9][C:8]=1[C:17]1[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:18]=1[F:25])=[CH2:6])([CH3:4])[CH3:3].[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>C1COCC1>[CH3:4][C:2]([C:5]([C:7]1[CH:12]=[C:11]([CH2:13][OH:14])[CH:10]=[CH:9][C:8]=1[C:17]1[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:18]=1[F:25])=[CH2:6])([CH3:1])[CH3:3]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 57705563HCID 57705563, compound

Product 1

HCID 57706195HCID 57706195, compoundYield 86.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 66.18F (0.400 g, 1 mmol) in THF (6 mL) at 0° C. was added LAH in THF (2 mL, 2 mmol, 1.0M). The resulting mixture was stirred for 2 hours. 1N NaOH(aq) was then added to the mixture, and the resulting mixture was extracted three times with EtOAc. After drying over anhydrous magnesium sulfate and filtering, the organic solvent was removed under reduced pressure and the product was then purified on silica gel (0-20% EtOAc in hexanes) to yield 66.18G as a colorless oil (0.273 g, 74% yield).

Workup

  1. extractionthe resulting mixture was extracted three times with EtOAc
  2. dry with materialAfter drying over anhydrous magnesium sulfate
  3. filtrationfiltering
  4. customthe organic solvent was removed under reduced pressure
  5. customthe product was then purified on silica gel (0-20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-21dc8ffc52bf452486b2aa5dc86f589d
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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