Tetrabutylammonium Fluoride → HCID 136395592, compound

HRID 2378047Notes

Reaction equation

HRID 2378047 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([CH2:27][OH:28])[CH2:26][CH2:25]3)[O:15][N:14]=2)=[CH:9][CH:8]=1)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[OH:28][CH2:27][C:24]1([C:16]2[O:15][N:14]=[C:13]([C:10]3[CH:11]=[CH:12][C:7]([OH:6])=[CH:8][CH:9]=3)[C:17]=2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:26][CH2:25]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59857621HCID 59857621, compound2×

Product 1

HCID 136395592HCID 136395592, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirring solution consisting of (1-{3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-4-phenyl-isoxazol-5-yl}-cyclopropyl)-methanol (compound E, Example 1) (18.2 g) in tetrahydrofuran (200 mL) at room temperature under a nitrogen atmosphere is added a 1.0 M solution consisting of tetrabutylammonium fluoride in tetrahydrofuran (45.3 mL.) The reaction mixture is stirred at room temperature overnight. The reaction mixture is concentrated under reduced pressure. The concentrate is purified by flash silica gel column chromatography. Elution with hexanes-ethyl acetate (1:1 v/v) afforded 12 g of a residue. The residue is dissolved in warm methanol. Addition of hexanes caused precipitation of a solid that is collected by filtration (11 g.) The solid is redissolved in warm methanol and again is precipitated with hexanes to afford a new crop of solid product (8.1 g); melting point 210-211° C.; MS (APCI+) m/z 308 (MH+.)

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. customThe concentrate is purified by flash silica gel column chromatography
  3. washElution with hexanes-ethyl acetate (1:1 v/v)

Sources & evidence

ORD record
ord-6200c7aecaf74ddd84a594ec25328424
Source dataset
uspto-grants-2008_12
Patent number
US07470715B2

Reaction notes

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