Lithium Hydroxide → HCID 25022352, compound

HRID 2101753Notes

Reaction equation

HRID 2101753 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]([C:34]#[C:35][CH3:36])[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]([C@@H:28]([C:34]#[C:35][CH3:36])[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 57672455HCID 57672455, compound

Product 1

HCID 25022352HCID 25022352, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4.2 (0.052 g, 0.11 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 purified by flash chromatography (SiO2 gel 60, eluted with 0%-20% EtOAc in hexanes) to give compound 4 as a clear oil (0.0466 g, 92% yield). 1H NMR (400 MHz, CDCl3) δ ppm 7.58 (1H, d, J=8.2 Hz), 7.41 (1H, dd, J=8.2, 2.0 Hz), 7.30 (2H, d, J=8.6 Hz), 7.08 (1H, d, J=2.0 Hz), 7.00 (1H, t, J=8.8 Hz), 6.93 (2H, d, J=8.6 Hz), 6.86 (1H, m), 6.80 (1H, dd, J=5.9, 3.3 Hz), 5.00 (2H, s), 4.06 (1H, m), 3.80 (3H, s), 2.81 (1H, dd, J=15.6, 8.4 Hz), 2.72 (1H, dd, J=15.6, 6.6 Hz), 1.84 (3H, d, J=2.3 Hz), 1.24 (9H, s). MS ESI (neg.) m/e: 947.3 (2M−H)+, 473.2 (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 purified by flash chromatography (SiO2 gel 60, eluted with 0%-20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-4c811b385da145a49d696ad5580c3053
Source dataset
uspto-grants-2009_08
Patent number
US07572934B2

Reaction notes

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