Ethanol → HCID 25057312, compound

HRID 2101797Notes

Reaction equation

HRID 2101797 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]([CH2:34][CH2:35][CH2:36][CH3:37])[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]([CH2:34][CH2:35][CH2:36][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 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 57672386HCID 57672386, compound

Product 1

HCID 25057312HCID 25057312, compoundYield 76%

Procedure

To a stirred solution of 30.1 (0.054 g, 0.11 mmol) in THF (2 mL, 0.2 mmol) and EtOH (2 mL, 0.2 mmol) at 23° C. was added a solution of 1 M sodium hydroxide (1.00 mL, 1.0 mmol). The resulting mixture was stirred for 19 hours. The reaction was then concentrated in vacuo, and 1 N HCl was added to bring the pH to 1. The resulting mixture was extracted with EtOAc, dried over MgSO4, filtered, and concentrated. The resulting product was purified by silica gel flash chromatography (0-20% EtOAc/hexane) to afford compound 30 (40 mg, 76% yield) as a colorless oil. MS ESI (neg.) m/e: 983.5 (2M−H)+, 491.2 (M−H)+.

Workup

  1. concentrationThe reaction was then concentrated in vacuo, and 1 N HCl
  2. additionwas added
  3. extractionThe resulting mixture was extracted with EtOAc
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting product was purified by silica gel flash chromatography (0-20% EtOAc/hexane)

Sources & evidence

ORD record
ord-403bdae88f38463f9f528b78e18df39f
Source dataset
uspto-grants-2009_08
Patent number
US07572934B2

Reaction notes

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