Hydrochloric Acid → HCID 123705153, compound

HRID 2231775Notes

Reaction equation

HRID 2231775 reaction equation
[CH3:1][SiH:2]([C:22]1[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]=1)[C:3]1[CH:8]=[C:7]([C:9]([CH3:12])([CH3:11])[CH3:10])[C:6]([O:13][Si](C)(C)C)=[C:5]([C:18]([CH3:21])([CH3:20])[CH3:19])[CH:4]=1.O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.Cl>O1CCCC1>[CH3:1][SiH:2]([C:3]1[CH:4]=[C:5]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:6]([OH:13])=[C:7]([C:9]([CH3:12])([CH3:11])[CH3:10])[CH:8]=1)[C:22]1[CH:23]=[C:24]([C:37]([CH3:40])([CH3:38])[CH3:39])[C:25]([OH:32])=[C:26]([C:28]([CH3:30])([CH3:31])[CH3:29])[CH:27]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 123143456HCID 123143456, compound

Product 1

HCID 123705153HCID 123705153, compoundYield 59.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of 6.0 g (10 mmol) of methylbis (3,5-di-tert-butyl-4-trimethylsilyloxyphenyl)silane in 30 ml of tetrahydrofuran is added dropwise a solution of 6.3 g (20 mmol) of tetrabutylammonium fluoride trihydrate in 35 ml of tetrahydrofuran. A vigorous evolution of gas is witnessed during the addition and the reaction mixture becomes green in color. The reaction mixture is stirred for 5 minutes at room temperature and to it is added dropwise a solution of 1.9 g (52 mmol) of concentrated hydrochloric acid in 10 ml of tetrahydrofuran. The solvent is removed in vacuo and the residue is recrystallized from n-propyl alcohol to give 2.7 grams of white solid which is a mixture of two products. The product mixture is separated by preparative HPLC (silica gel, 99:1, heptane, ethyl acetate) to give 0.4 g (9%) of the desired product as white crystals; mp. 191°-193.5° C.

Workup

  1. additionA vigorous evolution of gas is witnessed during the addition
  2. customThe solvent is removed in vacuo
  3. customthe residue is recrystallized from n-propyl alcohol

Sources & evidence

ORD record
ord-1f828847646242c9b8293bcfb0f43554
Source dataset
uspto-grants-1988_11
Patent number
US04783495

Reaction notes

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