Tetrabutylammonium Fluoride → 4-[2-(2-{2-[2-(2-Trityloxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]phenol

HRID 2075632Notes

Reaction equation

HRID 2075632 reaction equation
C([Si](C)(C)[O:6][C:7]1[CH:12]=[CH:11][C:10]([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:9][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:10]1[CH:11]=[CH:12][C:7]([OH:6])=[CH:8][CH:9]=1)([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=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 23080801Tert-butyl-dimethyl-{4-[2-(2-{2-[2-(2-trityloxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-phenoxy}silane

Product 1

HCID 670893454-[2-(2-{2-[2-(2-Trityloxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]phenolYield 92.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To an ice-cooled solution of Compound 21 (1.88 g, 2.74 mmol) in THF (20 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 10 minutes. This was poured over water to stop the reaction, after which extraction from ethyl acetate was conducted. The organic phases were combined, washed with saturated brine, thereafter dried with anhydrous sodium sulfate. After filtration and concentration under reduced pressure, the residue obtained was purified by silica gel column chromatography (Yamazen YFLC Gel, eluent (n-hexane:ethyl acetate 2:1-1:1)) to yield Compound 22 (light-yellow oil 1.45 g, 92%).

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. filtrationAfter filtration and concentration under reduced pressure
  9. customthe residue obtained
  10. customwas purified by silica gel column chromatography (Yamazen YFLC Gel, eluent (n-hexane:ethyl acetate 2:1-1:1))

Sources & evidence

ORD record
ord-7e5ca215343e4e678790405037220311
Source dataset
uspto-grants-2011_04
Patent number
US07919653B2

Reaction notes

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