Ethanol → HCID 25056273, compound

HRID 2101772Notes

Reaction equation

HRID 2101772 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:35]([CH3:37])=[CH2:36])[CH2:29][C:30]([O:32]CC)=[O:31])=[CH:24][CH:23]=2)=[CH:7][CH:6]=1)([CH3:4])[CH3:3].CCO.C1COCC1.[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]([C:35]([CH3:37])=[CH2:36])[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 57672447HCID 57672447, compound

Product 1

HCID 25056273HCID 25056273, compoundYield 74.8%

Procedure

To a stirred solution of 15.6 (0.044 g, 0.087 mmol) in EtOH (2.00 mL, 0.087 mmol) and THF (2.00 mL, 0.087 mmol) at 23° C. was added a solution of 1M sodium hydroxide (1.00 mL, 1.0 mmol). Stirring was continued for 18 hours. The resulting reaction was concentrated in vacuo. 1N HCl was added to pH 1, the resulting mixture was extracted EtOAc, dried over MgSO4, and concentrated. The crude product was purified by silica gel flash chromatography (0-20% EtOAc/hexane) to afford compound 15 (31 mg, 74% yield) as a colorless oil. MS ESI (neg.) m/e: 951.4 (2M−H)+, 475.1 (M−H)+.

Workup

  1. customThe resulting reaction
  2. concentrationwas concentrated in vacuo
  3. addition1N HCl was added to pH 1
  4. extractionthe resulting mixture was extracted EtOAc
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe crude product was purified by silica gel flash chromatography (0-20% EtOAc/hexane)

Sources & evidence

ORD record
ord-d12b91eff0ca4ee1b56f3d8476669fed
Source dataset
uspto-grants-2009_08
Patent number
US07572934B2

Reaction notes

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