Ethanol → HCID 25055751, compound

HRID 2101750Notes

Reaction equation

HRID 2101750 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].C1COCC1.CCO.[OH-].[Li+]>>[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 4

HCID 702EthanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 57672471HCID 57672471, compound

Product 1

HCID 25055751HCID 25055751, compoundYield 94%

Procedure

To a stirred solution of 1.1 (0.050 g, 0.099 mmol) in THF (2.00 mL, 24 mmol) and EtOH (2.00 mL, 34 mmol) at 23° C. was added 1N lithium hydroxide (1.00 mL, 1.0 mmol). Stirring was continued for 22 hours. The reaction 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 (0.0443 g, 94% yield). 1H NMR (400 MHz, CDCl3) δ ppm 7.58 (1H, d, J=8.6 Hz), 7.40 (1H, dd, J=8.2, 2.0 Hz), 7.13 (2H, d, J=8.6 Hz), 7.08 (1H, d, J=1.5 Hz), 7.00 (1H, t, J=8.8 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, 7.6 Hz), 2.71 (2H, dd, J=7.6, 2.5 Hz), 1.66 (3H, d, J=5.9 Hz), 1.23 (9H, m). MS ESI (neg.) m/e: 951.4.1 (2M−H)+, 475.1 (M−H)+.

Workup

  1. concentrationThe reaction 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-bfd2e08e736f4c4eb099c66d7d0dd024
Source dataset
uspto-grants-2009_08
Patent number
US07572934B2

Reaction notes

Loading…