Ethyl Acetate → HCID 136395601, compound

HRID 2378075Notes

Reaction equation

HRID 2378075 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:30])[CH2:28][CH3:29])[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:30][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)[CH2:28][CH3:29]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 162116731-Butanaminium, N,N,N-tributyl-, fluoride, hydrateHCID 68959536HCID 68959536, compound

Product 1

HCID 136395601HCID 136395601, 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}-cyclopropyl)-propan-1-ol, which may be produced as in Example 174 (2.1 g) in 60 mL of anhydrous THF is added tetrabutylammonium fluoride hydrate (2.4 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 is 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 was purified by flash chromatography (silica gel, 40% ethyl acetate in hexane) to afford the white solid (±)-4-{5-{1-(1-hydroxy-propyl)-cyclopropyl]-4-phenyl-isoxazol-3-yl}-phenol; MS (APCI+) m/z 336 (MH+.)

Workup

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

Sources & evidence

ORD record
ord-775e8d30fab249dfbb29c14d2836aa84
Source dataset
uspto-grants-2008_12
Patent number
US07470715B2

Reaction notes

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