Hydrochloric Acid → HCID 21285700, compound

HRID 2231776Notes

Reaction equation

HRID 2231776 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([Si:20]([C:41]2[CH:46]=[C:45]([C:47]([CH3:50])([CH3:49])[CH3:48])[C:44]([O:51][Si](C)(C)C)=[C:43]([C:56]([CH3:59])([CH3:58])[CH3:57])[CH:42]=2)([C:22]2[CH:27]=[C:26]([C:28]([CH3:31])([CH3:30])[CH3:29])[C:25]([O:32][Si](C)(C)C)=[C:24]([C:37]([CH3:40])([CH3:39])[CH3:38])[CH:23]=2)[OH:21])[CH:8]=[C:9]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:10]=1[O:11][Si](C)(C)C)([CH3:4])([CH3:3])[CH3:2].O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.Cl>O1CCCC1>[C:37]([C:24]1[CH:23]=[C:22]([Si:20]([C:41]2[CH:42]=[C:43]([C:56]([CH3:59])([CH3:58])[CH3:57])[C:44]([OH:51])=[C:45]([C:47]([CH3:50])([CH3:49])[CH3:48])[CH:46]=2)([C:7]2[CH:8]=[C:9]([C:16]([CH3:17])([CH3:18])[CH3:19])[C:10]([OH:11])=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:6]=2)[OH:21])[CH:27]=[C:26]([C:28]([CH3:31])([CH3:29])[CH3:30])[C:25]=1[OH:32])([CH3:38])([CH3:39])[CH3:40]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 14274483HCID 14274483, compound

Product 1

HCID 21285700HCID 21285700, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 0.40 g (0.45 mmol) of tris-(3,5-di-tert-butyl-4-trimethylsilyloxyphenyl)hydroxysilane in 3 ml of tetrahydrofuran at 0° C. is added dropwise a solution of 0.43 g (1.37 mmol) of tetrabutylammonium fluoride trihydrate in 3 ml of tetrahydrofuran. The reaction mixture is stirred for 5 minutes at 0° C. and to it is added dropwise a solution of 0.19 g of concentrated hydrochloric acid in 1 ml of tetrahydrofuran. The solvent is removed in vacuo and the residue is dissolved in 30 ml of diethylether. The solution is extracted (3×25 ml) with water. The organic phase is dried over anhydrous sodium sulfate and the solvent is removed in vacuo to give 0.29 g of a white amorphous solid. The crude product is purified by preparative thin layer chromatography (silica gel, 7:3, heptane:ethyl acetate eluent) followed by crystallization from a heptane/toluene solvent mixture to give 0.14 g (46%) of product as a white solid; mp. 257°-258 ° C.

Workup

  1. customThe solvent is removed in vacuo
  2. dissolutionthe residue is dissolved in 30 ml of diethylether
  3. extractionThe solution is extracted (3×25 ml) with water
  4. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  5. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-d10461ae8e0e45a29400dff79b68e505
Source dataset
uspto-grants-1988_11
Patent number
US04783495

Reaction notes

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