Pyridine → HCID 54082292, compound

HRID 1977439Notes

Reaction equation

HRID 1977439 reaction equation
[Si:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[C:15]([O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[CH:16]=1)[CH2:12][OH:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:25](Cl)(=[O:29])[C:26]([CH3:28])=[CH2:27].N1C=CC=CC=1>CCOCC>[C:25]([O:13][CH2:12][C:11]1[CH:10]=[C:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH:16]=[C:15]([O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:19])[CH3:20])[CH:14]=1)(=[O:29])[C:26]([CH3:28])=[CH2:27]

Participants

5

Reactant 3

HCID 1049PyridineHCID 13528Methacryloyl chlorideHCID 13499466HCID 13499466, compound

Product 1

HCID 54082292HCID 54082292, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

3,5-Di-tert-butyldimethylsilyloxybenzyl alcohol (13.0 g, 35.2 mmole) and freshly distilled methacryloyl chloride (4.06 g, 38.8 mmole) were dissolved in 75 ml of ether and cooled to 0° C. Pyridine (3.21 g, 40.6 mmole) in ether (10 ml) was added dropwise and the reaction mixture was stirred overnight at room temperature. The pyridinium hydrochloride was filtered off and the filtrate was passed over a silica bed to remove the traces of methacrylic acid. Through the silica bed were passed another 75 ml of ether, and after combination of the fractions, the ether was removed under reduced pressure to obtain an oily product (14.2 g, 32.7 mmole, 93%).

Workup

  1. filtrationThe pyridinium hydrochloride was filtered off
  2. customto remove the traces of methacrylic acid
  3. customafter combination of the fractions, the ether was removed under reduced pressure

Sources & evidence

ORD record
ord-4b578c66852c42f09ac8e369a63d9125
Source dataset
uspto-grants-2001_05
Patent number
US06232430B1

Reaction notes

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