HCID 59457726, compound → HCID 59457678, compound

HRID 1711092Notes

Reaction equation

HRID 1711092 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]#[C:9][Si](C)(C)C)[C:3]=1[CH2:14][C:15]([O:17]CC)=[O:16]>[OH-].[Na+].CO>[C:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=1[CH2:14][C:15]([OH:17])=[O:16])#[CH:9]

Participants

4

Reactant 1

HCID 59457726HCID 59457726, compound

Product 1

HCID 59457678HCID 59457678, compoundYield 103%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A stirred solution of 331 (607 mg, 2.18 mmol) and IN NaOH (5.5 mL) in methanol (15 mL) was heated at 45° C. for 16 h under nitrogen. The reaction mixture was allowed to cool to room temperature; it was then concentrated, diluted with water, and washed with hexanes. The aqueous layer was collected, acidified with 3N HCl and extracted twice with AcOEt. The organic extract was dried over anhydrous magnesium sulfate, filtered, and concentrated to afford title compound 332 (400 mg, 94% yield, mono-hydrate) as an orange sticky solid. LCMS: 201.1 (M+Na)+.

Workup

  1. concentrationit was then concentrated
  2. additiondiluted with water
  3. washwashed with hexanes
  4. customThe aqueous layer was collected
  5. extractionextracted twice with AcOEt
  6. extractionThe organic extract
  7. dry with materialwas dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-cae76e8cfe544fb4bc83698de2325227
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

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