Sodium Hydroxide → HCID 57706041, compound

HRID 1662447Notes

Reaction equation

HRID 1662447 reaction equation
[CH3:1][C:2]1([CH3:28])[C:6]([C:7]2[CH:12]=[C:11]([C:13](OC)=[O:14])[CH:10]=[CH:9][C:8]=2[C:17]2[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:19][C:18]=2[F:27])=[CH:5][CH2:4][CH2:3]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>C1COCC1>[CH3:1][C:2]1([CH3:28])[C:6]([C:7]2[CH:12]=[C:11]([CH2:13][OH:14])[CH:10]=[CH:9][C:8]=2[C:17]2[CH:22]=[C:21]([C:23]([F:24])([F:25])[F:26])[CH:20]=[CH:19][C:18]=2[F:27])=[CH:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 57706183HCID 57706183, compound

Product 1

HCID 57706041HCID 57706041, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled solution of 66.53A (0.4142 g, 1.056 mmol) in dry THF (7.8 mL) at 0° C. was added LAH (1.0 M in THF) (2.2 mL, 2.200 mmol) dropwise. Upon complete addition, the reaction was maintained at 0° C. and was monitored by TLC and LCMS. After 45 minutes, 1N NaOH was added to quench the reaction (gas evolution occurred). The resulting solution was extracted three times with EtOAc. After drying over anhydrous magnesium sulfate, filtration, and concentration, the residue was purified by flash chromatography (SiO2 gel 60, eluted with 0%-100% EtOAc in hexanes). Fractions containing the desired product were combined and concentrated to afford 66.53B as a colorless oil (257.4 mg, 67% yield). 1H NMR (400 MHz, CDCl3) δ ppm 7.61 (2H, m), 7.40 (2H, m), 7.17 (1H, t, J=8.8 Hz), 5.52 (1H, m), 4.77 (2H, s), 2.24 (2H, td, J=7.0, 2.3 Hz), 1.71 (3H, m), 0.84 (6H, s).

Workup

  1. additionUpon complete addition
  2. customto quench
  3. customthe reaction (gas evolution occurred)
  4. extractionThe resulting solution was extracted three times with EtOAc
  5. dry with materialAfter drying over anhydrous magnesium sulfate, filtration, and concentration
  6. customthe residue was purified by flash chromatography (SiO2 gel 60, eluted with 0%-100% EtOAc in hexanes)
  7. additionFractions containing the desired product
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-ef4473ebda8c42ae9798016df5e27627
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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