Lithium Hydroxide → HCID 25056010, compound

HRID 2101751Notes

Reaction equation

HRID 2101751 reaction equation
[CH3:1][C:2]([C:5]1[C:10]([C:11]2[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:12]=2[F:19])=[CH:9][C:8]([CH2:20][O:21][C:22]2[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][C:30]([O:32]C)=[O:31])=[CH:24][CH:23]=2)=[CH:7][CH:6]=1)([CH3:4])[CH3:3].[OH-].[Li+]>C1COCC1.CCO>[CH3:4][C:2]([C:5]1[C:10]([C:11]2[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:12]=2[F:19])=[CH:9][C:8]([CH2:20][O:21][C:22]2[CH:23]=[CH:24][C:25]([CH2:28][CH2:29][C:30]([OH:32])=[O:31])=[CH:26][CH:27]=2)=[CH:7][CH:6]=1)([CH3:1])[CH3:3]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 57672422HCID 57672422, compound

Product 1

HCID 25056010HCID 25056010, compoundYield 83.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2.2 (0.0421 g, 0.0934 mmol) in THF (2.00 mL) and EtOH (2.00 mL) at 23° C. was added 1N lithium hydroxide (2.00 mL, 2.00 mmol). Stirring continued for 16 hours. The reaction mixture was concentrated in vacuo. 1N HCl was added to reach pH 1, and the resulting mixture was extracted with EtOAc (3×10 mL), dried over MgSO4 and concentrated in vacuo. The residue was then purified by flash chromatography (SiO2 gel 60, eluted with 0%-20% EtOAc in hexanes) to give a clear oil (0.034 g, 82% yield). 1H NMR (400 MHz, CDCl3) δ ppm 7.59 (1H, d, J=8.2 Hz), 7.41 (1H, dd, J=8.6, 2.2 Hz), 7.22 (1H, dd, J=9.0, 7.4 Hz), 7.11 (1H, d, J=2.2 Hz), 7.00 (1H, t, J=8.6 Hz), 6.88-6.79 (5H, m), 5.01 (2H, s), 3.79 (3H, s), 2.94 (2H, t, J=7.8 Hz), 2.68 (2H, t, J=7.8 Hz), 1.24 (9H, s). MS ESI (neg.) m/e: 871.3 (2M−H)+, 435.1 (M−H)+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. addition1N HCl was added
  3. extractionthe resulting mixture was extracted with EtOAc (3×10 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was then purified by flash chromatography (SiO2 gel 60, eluted with 0%-20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-10418dd77cc140f9aaccbd0f8ba41105
Source dataset
uspto-grants-2009_08
Patent number
US07572934B2

Reaction notes

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