Ethanol → HCID 25056532, compound

HRID 2101774Notes

Reaction equation

HRID 2101774 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 57672513HCID 57672513, compound

Product 1

HCID 25056532HCID 25056532, compoundYield 79.5%

Procedure

To a stirred solution of 17.2 (0.048 g, 0.095 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 1 M sodium hydroxide (1.00 mL, 1.0 mmol). Stirring was continued for 18 hours. The resulting reaction was concentrated in vacuo. 1 N HCl was added to bring the pH to 1, and the resulting mixture was extracted with EtOAc, dried over MgSO4, and concentrated. The crude product was purified by silica gel flash chromatography (0-20% EtOAc/hexane) to afford compound 17 (36 mg, 79% yield) as a colorless oil. MS ESI (neg.) m/e: 475.1 (M−H)+.

Workup

  1. customThe resulting reaction
  2. concentrationwas concentrated in vacuo
  3. addition1 N HCl was added
  4. extractionthe resulting mixture was extracted with 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-0a4cc7ccac7546d5ae84792c1807bf90
Source dataset
uspto-grants-2009_08
Patent number
US07572934B2

Reaction notes

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