Ethyl Acetate → HCID 135899257, compound

HRID 2378074Notes

Reaction equation

HRID 2378074 reaction equation
C([Si](C)(C)[O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:16]([C:24]3([CH:27]([OH:29])[CH3:28])[CH2:26][CH2:25]3)[O:15][N:14]=2)=[CH:9][CH:8]=1)(C)(C)C.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[NH4+].C(OCC)(=O)C>C1COCC1>[OH:29][CH:27]([C:24]1([C:16]2[O:15][N:14]=[C:13]([C:10]3[CH:9]=[CH:8][C:7]([OH:6])=[CH:12][CH:11]=3)[C:17]=2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:26][CH2:25]1)[CH3:28]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 162116731-Butanaminium, N,N,N-tributyl-, fluoride, hydrateHCID 68955835HCID 68955835, compound

Product 1

HCID 135899257HCID 135899257, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (±)-1-(1-{3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-4-phenyl-isoxazol-5-yl}-cyclopropy)-ethanol, which may be produced as in Example 178A (2.2 g) in 60 mL of anhydrous THF is added tetrabutylammonium fluoride hydrate (2.6 g.) The reaction mixture is stirred at room temperature for 4 hrs. Saturated ammonium chloride (50 mL) is added to the reaction mixture, followed with 300 mL of ethyl acetate. The aqueous layer are separated and then the organic layer is washed with additional saturated ammonium chloride (2×50 mL), followed with brine (50 mL). The organic layer is dried (sodium sulfate), filtered, and the filtrate is evaporated to give a white solid, which is purified by flash chromatography (silica gel, 40% ethyl acetate in hexane) to afford a white solid as (±)-4-{5-{1-(1-hydroxy-ethyl)-cyclopropyl]-4-phenyl-isoxazol-3-yl}-phenol.

Workup

  1. customThe aqueous layer are separated
  2. washthe organic layer is washed with additional saturated ammonium chloride (2×50 mL)
  3. dry with materialThe organic layer is dried (sodium sulfate)
  4. filtrationfiltered
  5. customthe filtrate is evaporated
  6. customto give a white solid, which
  7. customis purified by flash chromatography (silica gel, 40% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-d3402a193c5e469dac3dd4ae41682650
Source dataset
uspto-grants-2008_12
Patent number
US07470715B2

Reaction notes

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