Ethanol → HCID 44232533, compound

HRID 1257457Notes

Reaction equation

HRID 1257457 reaction equation
[F:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:12]1[N:13]=[C:14]([CH2:17][C:18]2[CH:27]=[CH:26][C:21]([C:22]([O:24]C)=[O:23])=[CH:20][CH:19]=2)[S:15][CH:16]=1.C(O)C.[OH-].[Na+]>O1CCCC1>[F:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:12]1[N:13]=[C:14]([CH2:17][C:18]2[CH:27]=[CH:26][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=2)[S:15][CH:16]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 66939152HCID 66939152, compound

Product 1

HCID 44232533HCID 44232533, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the compound (300 mg, 0.759 mmol) obtained in Example 186b were added ethanol (4 mL), tetrahydrofuran (2 mL) and 2N aqueous sodium hydroxide solution (0.76 mL, 1.52 mmol), and the mixture was stirred overnight. The reaction mixture was extracted with water, and washed with ether. The aqueous layer was acidified with 6N hydrochloric acid, and extracted with ethyl acetate. The extract was washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (carrier: silica gel, eluent: hexane-ethyl acetate), and recrystallized from ethanol-hexane to give the title compound (186 mg, 64%) as colorless crystals.

Workup

  1. extractionThe reaction mixture was extracted with water
  2. washwashed with ether
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography (carrier: silica gel, eluent: hexane-ethyl acetate)
  8. customrecrystallized from ethanol-hexane

Sources & evidence

ORD record
ord-41f48e932f914a1ea9d343ebb905b2a8
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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