Ethanol → HCID 57672379, compound

HRID 2101759Notes

Reaction equation

HRID 2101759 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:34]=[CH: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].C1COCC1.CCO.[OH-].[Na+]>>[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:34]=[CH: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 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 57672434HCID 57672434, compound

Product 1

HCID 57672379HCID 57672379, compoundYield 74%

Procedure

To a stirred solution of 8.1 (0.0529 g, 0.11 mmol) in THF (2.00 mL, 24 mmol) and EtOH (2.00 mL, 34 mmol) at 23° C. was added 1N sodium hydroxide (2.00 mL, 2.0 mmol). Stirring continued for 17 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 compound 8 as a clear oil (0.0382 g, 74% yield). 1H NMR (400 MHz, CDCl3) δ ppm 7.58 (1H, d, J=8.2 Hz), 7.40 (1H, dd, J=8.2, 2.0 Hz), 7.16 (2H, d, J=9.0 Hz), 7.08 (1H, d, J=2.0 Hz), 7.00 (1H, t, J=8.8 Hz), 6.92 (2H, d, J=9.0 Hz), 6.87 (1H, dt, J=8.9, 3.9 Hz), 6.80 (1H, m), 5.58-5.49 (2H, m), 4.99 (2H, s), 4.14 (1H, m), 3.79 (3H, s), 2.75 (1H, dd, J=15.1, 6.8 Hz), 2.64 (1H, dd, J=15.1, 8.6 Hz), 1.66 (3H, d, J=5.1 Hz), 1.23 (9H, s). 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-566e14e9e9cc45ea9bbbab4627bf29ed
Source dataset
uspto-grants-2009_08
Patent number
US07572934B2

Reaction notes

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