Ethanol → HCID 25056272, compound

HRID 2101773Notes

Reaction equation

HRID 2101773 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]=[C:35]([CH3:37])[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]=[C:35]([CH3:37])[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 57672427HCID 57672427, compound

Product 1

HCID 25056272HCID 25056272, compoundYield 86.1%

Procedure

To a stirred solution of 16.2 (0.047 g, 0.09 mmol) in THF (2.00 mL, 0.10 mmol) and EtOH (2.00 mL, 0.10 mmol) at 23° C. was added a 1 M solution of sodium hydroxide (1 mL, 1 mmol). Stirring was continued for 15 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 14 (38 mg, 82% yield) as a colorless oil. MS ESI (neg.) m/e: 489.2 (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-892142609bd04e6c8f534a856fa49714
Source dataset
uspto-grants-2009_08
Patent number
US07572934B2

Reaction notes

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