Pyridine → HCID 11256949, compound

HRID 988058Notes

Reaction equation

HRID 988058 reaction equation
[C:1](Cl)(=[O:5])[C:2]([CH3:4])=[CH2:3].[CH3:7][Si:8]([Si:11]([Si:19]([CH3:22])([CH3:21])[CH3:20])([Si:15]([CH3:18])([CH3:17])[CH3:16])[CH2:12][CH2:13][OH:14])([CH3:10])[CH3:9].N1C=CC=CC=1>O1CCCC1.C1C2NC3C(=CC=CC=3)SC=2C=CC=1>[C:1]([O:14][CH2:13][CH2:12][Si:11]([Si:19]([CH3:22])([CH3:21])[CH3:20])([Si:15]([CH3:18])([CH3:17])[CH3:16])[Si:8]([CH3:7])([CH3:9])[CH3:10])(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

6

Reactant 3

HCID 1049PyridineHCID 13528Methacryloyl chlorideHCID 133081222-[1,1,1,3,3,3-Hexamethyl-2-(trimethylsilyl)trisilan-2-yl]ethan-1-ol

Product 1

HCID 11256949HCID 11256949, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 7108PhenothiazineCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

Methacryloyl chloride (2.50 grams, 0.024 mole) in 25 ml tetrahydro-furan was added dropwise into a solution of 2-tris(trimethylsilyl) silyl ethanol (6.5 grams, 0.022 mole), pyridine (2.0 grams, 0.025 mole) and 25 mg of phenothiazine in 50 ml tetrahydrofuran at room temperature. Stirred at room temperature for two more hours. The solids were filtered off and the solution was washed with 100 ml brine. The solution was then diluted with 100 ml ether and washed with 5% hydrochloric acid, followed by deionized water, and then with brine. It was dried over anhydrous magnesium sulfate and was concentrated in vacuo. Fractional distillation under reduced pressed gave 5 grams of the product at 105-115° C. at 0.5 mm.

Workup

  1. filtrationThe solids were filtered off
  2. washthe solution was washed with 100 ml brine
  3. additionThe solution was then diluted with 100 ml ether
  4. washwashed with 5% hydrochloric acid
  5. dry with materialIt was dried over anhydrous magnesium sulfate
  6. concentrationwas concentrated in vacuo
  7. distillationFractional distillation

Sources & evidence

ORD record
ord-d5cbeb0a93d6451d95cf286ad45a1f7c
Source dataset
uspto-grants-2003_10
Patent number
USRE038282E1

Reaction notes

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