Ethanol → HCID 57672442, compound

HRID 2101800Notes

Reaction equation

HRID 2101800 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]=[CH: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](/[CH:34]=[CH: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 57672392HCID 57672392, compound

Product 1

HCID 57672442HCID 57672442, compoundYield 71.3%

Procedure

To a stirred solution of 34.2 (0.050 g, 0.10 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 reaction mixture was stirred for 21 hours, and concentrated in vacuo. 1 N HCl was added to bring the pH to 1, and the resulting mixture was extracted EtOAc, dried over MgSO4, filtered, and concentrated. The resulting product was purified by silica gel flash chromatography (0-20% EtOAc/hexane) to afford compound 34 (35 mg, 71% yield) as a colorless oil. MS ESI (neg.) m/e: 979.5 (2M−H)+, 489.2 (M−H)+.

Workup

  1. customThe resulting reaction mixture
  2. concentrationconcentrated in vacuo
  3. addition1 N HCl was added
  4. extractionthe resulting mixture was extracted EtOAc
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting product was purified by silica gel flash chromatography (0-20% EtOAc/hexane)

Sources & evidence

ORD record
ord-82f5a153b216494d92135ba518499e25
Source dataset
uspto-grants-2009_08
Patent number
US07572934B2

Reaction notes

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