Lithium Hydroxide → HCID 25055750, compound

HRID 2101752Notes

Reaction equation

HRID 2101752 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]([C@@H:28](/[CH:35]=[CH:36]/[CH3:37])[CH2:29][C:30]([O:32]CC)=[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]([C@@H:28](/[CH:35]=[CH:36]/[CH3:37])[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 57672431HCID 57672431, compound

Product 1

HCID 25055750HCID 25055750, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3.2 (0.0313 g, 0.062 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 20 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 (0.0241 g, 82% yield). 1H NMR (400 MHz, CDCl3) δ ppm 7.58 (I H, d, J=8.2 Hz), 7.40 (1H, dd, J=8.4, 2.2 Hz), 7.13 (2H, d, J=8.6 Hz), 7.08 (1H, d, J=1.5 Hz), 7.00 (1H, t, J=8.6 Hz), 6.92 (2H, d, J=8.6 Hz), 6.86 (1H, m), 6.79 (1H, m), 5.57 (1H, m), 5.50 (1H, m), 4.99 (2H, s), 3.79 (3H, s), 3.76 (1H, dd, J=14.5, 7.8 Hz), 2.71 (2H, dd, J=7.8, 2.3 Hz), 1.66 (3H, d, J=6.3 Hz), 1.23 (9H, m). MS ESI (neg.) m/e: 951.4 (2M−H)+, 475.1 (M−H)+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo, 1N HCl
  2. additionwas 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-1d3c0503365148d7b083dbee65ace648
Source dataset
uspto-grants-2009_08
Patent number
US07572934B2

Reaction notes

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