Sodium Hydroxide → HCID 57707246, compound

HRID 1662344Notes

Reaction equation

HRID 1662344 reaction equation
[CH3:1][C:2]([C:5]1[CH:10]=[C:9]([C:11](OC)=[O:12])[CH:8]=[CH:7][C:6]=1[C:15]1[CH:20]=[C:19]([O:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][O:23]2)[CH:18]=[CH:17][C:16]=1[F:28])([CH3:4])[CH3:3].[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>C1COCC1>[CH3:4][C:2]([C:5]1[CH:10]=[C:9]([CH2:11][OH:12])[CH:8]=[CH:7][C:6]=1[C:15]1[CH:20]=[C:19]([O:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][O:23]2)[CH:18]=[CH:17][C:16]=1[F:28])([CH3:1])[CH3:3]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 57705716HCID 57705716, compound

Product 1

HCID 57707246HCID 57707246, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled solution of 35.2 (0.080 g, 0.30 mmol) in THF (3.00 mL) at 0° C., was added LAH (1.0 M solution in THF, 0.60 mL, 0.60 mmol). Stirring was continued for 1 hour. 1N NaOH (5 mL) was carefully added to quench the reaction. The resulting solution was extracted with EtOAc (3×10 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. The residue was then purified by flash chromatography (SiO2 gel 60, eluted with 0%-30% EtOAc in hexanes). Fractions containing the desired product were combined and concentrated to provide 35.3 as a colorless oil (0.055 g, 54%). MS ESI (pos.) m/e: 739.3 (2M+Na)+, 376.1 (M+H2O)+.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionThe resulting solution was extracted with EtOAc (3×10 mL)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was then purified by flash chromatography (SiO2 gel 60, eluted with 0%-30% EtOAc in hexanes)
  8. additionFractions containing the desired product
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-6f2246177b7b4c558c4785426098f4a6
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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