Sodium Hydroxide → HCID 57705618, compound

HRID 1662514Notes

Reaction equation

HRID 1662514 reaction equation
[CH:1]1([C:8]2[CH:13]=[C:12]([C:14](OC)=[O:15])[CH:11]=[CH:10][C:9]=2[C:18]2[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[CH:20][C:19]=2[F:26])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>C1COCC1>[CH:1]1([C:8]2[CH:13]=[C:12]([CH2:14][OH:15])[CH:11]=[CH:10][C:9]=2[C:18]2[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[CH:20][C:19]=2[F:26])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 57705779HCID 57705779, compound

Product 1

HCID 57705618HCID 57705618, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 78.7D (0.260 g, 0.7 mmol) in THF (7 mL) at 0° C. was added LAH (1 mL, 1 mmol, 1.0M). The reaction was stirred for one hour and then 1N NaOH was added to quench the reaction. The resulting solution 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 purified on silica gel (0-20% EtOAc in hexanes) to yield 78.7E as a colorless oil (0.192 g, 80% yield). MS ESI (pos.) m/e: 311.2 (M−OH)+.

Workup

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

Sources & evidence

ORD record
ord-88738dc3ea7e4db5ad3d811de055b15f
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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