Tetrabutylammonium Fluoride → 5-[2-(2-{2-[2-(2-Trityloxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-benzene-1,3-diol

HRID 2075647Notes

Reaction equation

HRID 2075647 reaction equation
C([Si](C)(C)[O:6][C:7]1[CH:12]=[C:11]([O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][C:29]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:10]=[C:9]([O:48][Si](C(C)(C)C)(C)C)[CH:8]=1)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:29]([O:28][CH2:27][CH2:26][O:25][CH2:24][CH2:23][O:22][CH2:21][CH2:20][O:19][CH2:18][CH2:17][O:16][CH2:15][CH2:14][O:13][C:11]1[CH:12]=[C:7]([OH:6])[CH:8]=[C:9]([OH:48])[CH:10]=1)([C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)([C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 670892321,3-Bis-(tert-butyl-dimethyl-silanyloxy)-5-[2-(2-{2-[2-(2-trityloxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-benzene

Product 1

HCID 670890515-[2-(2-{2-[2-(2-Trityloxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-benzene-1,3-diolYield 96.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To an ice-cooled solution of Compound 44 (2.81 g, 3.44 mmol) in THF (30 ml), a solution of 1M tetrabutylammonium fluoride in THF (4 ml) was added. After completion of the addition, the ice bath was removed, and this was followed by stirring at room temperature for 1 hour. This was poured over water to stop the reaction, after which extraction from ethyl acetate was conducted. The organic phases were combined and washed with saturated brine, thereafter dried with anhydrous sodium sulfate. Filtration and concentration under reduced pressure were conducted, after which the residue obtained was purified by silica gel column chromatography (Yamazen YFLC Gel, eluent (n-hexane:ethyl acetate 1:1-1:2-1:3)) to yield Compound 45 (light-yellow oil 1.95 g, 96%).

Workup

  1. additionAfter completion of the addition
  2. customthe ice bath was removed
  3. additionThis was poured over water
  4. customthe reaction
  5. extractionafter which extraction from ethyl acetate
  6. washwashed with saturated brine
  7. dry with materialdried with anhydrous sodium sulfate
  8. filtrationFiltration and concentration under reduced pressure
  9. customafter which the residue obtained
  10. customwas purified by silica gel column chromatography (Yamazen YFLC Gel, eluent (n-hexane:ethyl acetate 1:1-1:2-1:3))

Sources & evidence

ORD record
ord-bf38460cb8ec4dcabf0f14d2bf1a1283
Source dataset
uspto-grants-2011_04
Patent number
US07919653B2

Reaction notes

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